Updated on 2024/04/18

写真a

 
TATSUTA, Kuniaki
 
Affiliation
Faculty of Science and Engineering
Job title
Professor Emeritus
Degree
Doctor(Ph.D) ( Keio University )

Research Experience

  • 2004
    -
    　

    - 大学院理工学研究科長

  • 2004
    -
    　

    - Dean of Graduate School of Science and Engineering

  • 2000
    -
    2002

    応用化学科 主任教授

  • 2000
    -
    2002

    Chairman of Department of Applied Chemistry

Education Background

  • 　
    -
    1968

    Keio University  

  • 　
    -
    1968

    Keio University   Graduate School, Division of Engineering  

  • 　
    -
    1963

    Keio University  

  • 　
    -
    1963

    Keio University   Faculty of Engineering  

Committee Memberships

  • 2010
    -
    　

    日本化学会  副会長

  • 2004
    -
    　

    有機合成化学協会  副会長

  • 1998
    -
    2004

    日本化学会  理事

  • 1998
    -
    2000

    有機合成化学協会  理事

  • 1999
    -
    　

    有機合成化学協会  編集委員長

  • 1989
    -
    1991

    日本化学会  理事

  • 1988
    -
    1990

    有機合成化学協会  理事

  • 1978
    -
    　

    日本抗生物質学術協議会  評議員

▼display all

Professional Memberships

  • 　
    　
    　

    アメリカ化学会(American Chemical Society)

  • 　
    　
    　

    日本抗生物質学術協議会

  • 　
    　
    　

    有機合成化学協会

  • 　
    　
    　

    日本化学会

  • 　
    　
    　

    American Chemical Society

  • 　
    　
    　

    Japan Antibiotics Research Association

  • 　
    　
    　

    Synthetic Organic Chemistry Japan

  • 　
    　
    　

    The Chemical Society of Japan

▼display all

Research Areas

  • Synthetic organic chemistry

Research Interests

  • 有機合成化学

  • 生理活性物質化学

  • 有機工業化学

  • Synthetic Organic Chemistry

  • Bioactive Substances Science

Awards

  • 日本学士院賞

    2009  

  • Japan Academy Prize

    2009  

  • 藤原賞（藤原科学財団）

    2008  

  • 大隈記念学術褒賞

    2008  

  • Fujihara Award (The Fujihara Foundation of Science)

    2008  

  • Okuma Award

    2008  

  • 紫綬褒章

    2002  

  • Imperial Medal with Purple Ribbon of Japan (Emperor)

    2002  

  • 日本化学会賞

    2001  

  • Distinguished Award of The Chemical Society of Japan

    2001  

  • 有機合成化学協会賞

    1998  

  • Award of Synthetic Organic Chemistry Japan

    1998  

  • 大河内記念賞

    1991  

  • Oukouchi Award

    1991  

  • 日本抗生物質学術協議会住木・梅澤賞

    1988  

  • Sumiki - Umezawa Memorial Award of Japan Antibiotics Research Association

    1988  

  • 日本化学会学術賞

    1986  

  • Award of The Chemical Society of Japan

    1986  

  • 服部報公会報公賞

    1983  

  • Hoko - Prize of The Foundation “Hattori-Hokokai”

    1983  

▼display all

 

Research Projects

  • 有用な生理活性物質の工業的合成法の開発

  • 新規生理活性物質の開発

  • 天然生理活性物質の単離、構造決定

  • 生理活性物質の全合成

  • 生理活性物質科学

  • 天然物の合成研究

  • Bioactive Substances Science

  • Synthetic Studies on Natural Products

▼display all

Misc

  • The first total synthesis and structural determination of epi-cochlioquinone A

    Seijiro Hosokawa, Kaoru Matsushita, Shinpei Tokimatsu, Tatsuya Toriumi, Yasuaki Suzuki, Kuniaki Tatsuta

    TETRAHEDRON LETTERS   51 ( 42 ) 5532 - 5536  2010.10

    　View Summary

    The first total synthesis of epi-cochlioquinone A has been achieved in a highly convergent manner via [3+3] cycloaddition of catechol 2 and oxadecalin 3 as the key reaction. The synthesis of the catechol segment, possessing the side chain with multi stereogenic centers, features the asymmetric vinylogous Mukaiyama aldol reaction, the stereoselective conjugate addition to the nitroalkene, the stereospecific nitro-Dieckmann condensation, and the transformation of 6-nitrocyclohex-2-enone into catechol 2, using two new methodologies, such as (i) the hydrogen-transfer reaction to o-aminophenol and the subsequent auto-redox-catalysis to catechol and (ii) the direct oxidation of 6-nitrocyclohex-2-enone to o-quinone and the subsequent reduction. The oxadecalin segment was synthesized from a glycosyl cyanide by the [3+3] annulation with a ketone and an acetoacetate. These segments were connected by the [3+3] cyclization, and the resulting tetracyclic compound was subjected to a specific oxidation of the protected hydroquinone to provide epi-cochlioquinone A. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis of lactonamycin, a hexacyclic antitumor antibiotic

    Kuniaki Tatsuta, Hiroaki Tanaka, Hitomi Tsukagoshi, Takafumi Kashima, Seijiro Hosokawa

    TETRAHEDRON LETTERS   51 ( 42 ) 5546 - 5549  2010.10

    　View Summary

    The total synthesis of lactonamycin has been achieved. The synthesis includes sequential intramolecular conjugate addition of alcohols to the acetylenic ester, stereoselective glycosylation of the tertiary alcohol, and Michael-Dieckmann type cyclization with the thioester, by which the highly convergent route has been established. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis and structural determination of epi-cochlioquinone A

    Seijiro Hosokawa, Kaoru Matsushita, Shinpei Tokimatsu, Tatsuya Toriumi, Yasuaki Suzuki, Kuniaki Tatsuta

    TETRAHEDRON LETTERS   51 ( 42 ) 5532 - 5536  2010.10

    　View Summary

    The first total synthesis of epi-cochlioquinone A has been achieved in a highly convergent manner via [3+3] cycloaddition of catechol 2 and oxadecalin 3 as the key reaction. The synthesis of the catechol segment, possessing the side chain with multi stereogenic centers, features the asymmetric vinylogous Mukaiyama aldol reaction, the stereoselective conjugate addition to the nitroalkene, the stereospecific nitro-Dieckmann condensation, and the transformation of 6-nitrocyclohex-2-enone into catechol 2, using two new methodologies, such as (i) the hydrogen-transfer reaction to o-aminophenol and the subsequent auto-redox-catalysis to catechol and (ii) the direct oxidation of 6-nitrocyclohex-2-enone to o-quinone and the subsequent reduction. The oxadecalin segment was synthesized from a glycosyl cyanide by the [3+3] annulation with a ketone and an acetoacetate. These segments were connected by the [3+3] cyclization, and the resulting tetracyclic compound was subjected to a specific oxidation of the protected hydroquinone to provide epi-cochlioquinone A. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis of lactonamycin, a hexacyclic antitumor antibiotic

    Kuniaki Tatsuta, Hiroaki Tanaka, Hitomi Tsukagoshi, Takafumi Kashima, Seijiro Hosokawa

    TETRAHEDRON LETTERS   51 ( 42 ) 5546 - 5549  2010.10

    　View Summary

    The total synthesis of lactonamycin has been achieved. The synthesis includes sequential intramolecular conjugate addition of alcohols to the acetylenic ester, stereoselective glycosylation of the tertiary alcohol, and Michael-Dieckmann type cyclization with the thioester, by which the highly convergent route has been established. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • 抗腫瘍性抗生物質lactonamycinの全合成

    第98回有機合成シンポジウム    2010

  • ACAT阻害物質epi-cochlioquinone Aの全合成

    第98回有機合成シンポジウム    2010

  • The first total synthesis and structural determination of benzopyrenomycin

    Seijiro Hosokawa, Yuki Mukaeda, Ryo Kawahara, Kuniaki Tatsuta

    TETRAHEDRON LETTERS   50 ( 48 ) 6701 - 6704  2009.12

    　View Summary

    The first total synthesis and structural determination of benzopyrenomycin has been achieved. This synthesis contains remarkable transformations including cyclization to afford the benzanthrone skeleton, syn-selective vinylogous Mukaiyama aldol reaction, and radical cyclization with the benzanthrone attaching the iodoalkane chain. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis and structural determination of benzopyrenomycin

    Seijiro Hosokawa, Yuki Mukaeda, Ryo Kawahara, Kuniaki Tatsuta

    TETRAHEDRON LETTERS   50 ( 48 ) 6701 - 6704  2009.12

    　View Summary

    The first total synthesis and structural determination of benzopyrenomycin has been achieved. This synthesis contains remarkable transformations including cyclization to afford the benzanthrone skeleton, syn-selective vinylogous Mukaiyama aldol reaction, and radical cyclization with the benzanthrone attaching the iodoalkane chain. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis of nidulalin A, a dihydroxanthone possessing multiple bioactivities

    Kuniaki Tatsuta, Shusuke Yoshihara, Nobutaka Hattori, Shinpei Yoshida, Seijiro Hosokawa

    JOURNAL OF ANTIBIOTICS   62 ( 8 ) 469 - 470  2009.08

    Other  

    DOI CiNii

  • The first total synthesis of nidulalin A, a dihydroxanthone possessing multiple bioactivities

    Kuniaki Tatsuta, Shusuke Yoshihara, Nobutaka Hattori, Shinpei Yoshida, Seijiro Hosokawa

    JOURNAL OF ANTIBIOTICS   62 ( 8 ) 469 - 470  2009.08

    Other  

    DOI CiNii

  • TOTAL SYNTHESIS OF AN ENDOTHELIN CONVERTING ENZYME INHIBITOR, TMC-66

    Seijiro Hosokawa, Hitoshi Fumiyama, Hisato Fukuda, Tomohiro Fukuda, Masashi Seki, Kuniaki Tatsuta

    HETEROCYCLES   76 ( 1 ) 699 - 713  2008.09

    　View Summary

    The first total synthesis and structural determination of TMC-66, an ECE inhibitor, was achieved in short steps by efficient construction of two tricyclic segments and coupling reactions. The oxidative coupling with phenols attaching to electron-withdrawing groups was realized with a novel copper (II) reagent.

  • TOTAL SYNTHESIS OF AN ENDOTHELIN CONVERTING ENZYME INHIBITOR, TMC-66

    Seijiro Hosokawa, Hitoshi Fumiyama, Hisato Fukuda, Tomohiro Fukuda, Masashi Seki, Kuniaki Tatsuta

    HETEROCYCLES   76 ( 1 ) 699 - 713  2008.09

    　View Summary

    The first total synthesis and structural determination of TMC-66, an ECE inhibitor, was achieved in short steps by efficient construction of two tricyclic segments and coupling reactions. The oxidative coupling with phenols attaching to electron-withdrawing groups was realized with a novel copper (II) reagent.

  • The first total synthesis and structural determination of TMC-264

    Kuniaki Tatsuta, Akiho Furuyama, Tomoe Yano, Yasuaki Suzuki, Takashi Ogura, Seijiro Hosokawa

    TETRAHEDRON LETTERS   49 ( 25 ) 4036 - 4039  2008.06

    　View Summary

    The first total synthesis and structural determination of TMC-264 has been accomplished. Regioselective bromination, regioselective methoxymethylation, and nickel(0)-Lewis acid-mediated cyclization afforded multi-functionalized 1-methyl-dibenzo[b,d]-pyran skeleton. (C) 2008 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis and structural determination of TMC-264

    Kuniaki Tatsuta, Akiho Furuyama, Tomoe Yano, Yasuaki Suzuki, Takashi Ogura, Seijiro Hosokawa

    TETRAHEDRON LETTERS   49 ( 25 ) 4036 - 4039  2008.06

    　View Summary

    The first total synthesis and structural determination of TMC-264 has been accomplished. Regioselective bromination, regioselective methoxymethylation, and nickel(0)-Lewis acid-mediated cyclization afforded multi-functionalized 1-methyl-dibenzo[b,d]-pyran skeleton. (C) 2008 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • FoxA1 as a lineage-specific oncogene in luminal type breast cancer

    Noritaka Yamaguchi, Emi Ito, Sakura Azuma, Reiko Honma, Yuka Yanagisawa, Akira Nishikawa, Mika Kawamura, Jun-ichi Imai, Kuniaki Tatsuta, Jun-ichiro Inoue, Kentaro Semba, Shinya Watanabe

    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS   365 ( 4 ) 711 - 717  2008.01

    　View Summary

    The forkhead transcription factor FoxA1 is thought to be involved in mammary tumorigenesis. However, the precise role of FoxA1 in breast cancer development is controversial. We examined expression of FoxA I in 35 human breast cancer cell lines and compared it with that of ErbB2, a marker of poor prognosis in breast cancer. We found that FoxA1 is expressed at high levels in all ErbB2-positive cell lines and a subset of ErbB2-negative cell lines. Down-regulation of FoxA1 by RNA interference significantly suppressed proliferation of ErbB2-negative and FoxA1-positive breast cancer cell lines. Down-regulation of FoxA1 also enhanced the toxic effect of Herceptin on ErbB2-positive cell lines through induction of apoptosis. Taken together with previous data that FoxA1 is a marker of luminal cells in mammary gland, our present results suggest that FoxA1 plays an important role as a lineage-specific oncogene in proliferation of cancer cells derived from mammary luminal cells. (c) 2007 Elsevier Inc. All rights reserved.

    DOI PubMed CiNii

  • Total Synthesis and Development of Bioactive Natural Products.

    K. Tatsuta

    Proc. Jpn. Acad., Ser. B   84 ( 4 ) 87 - 106  2008

    DOI

  • 多様な天然生理活性物質の全合成

    ＳＯＲＳＴジョイントシンポジウム    2008

  • Total Synthesis of Bioactive Products

    ETH seminer    2008

  • 多様な天然生理活性物質の全合成と開発

    第55回有機合成化学協会関東支部シンポジウム    2008

  • Learn from nature, and go beyond it - Medicinal developments

    ASMeW International Symposium    2008

  • FoxA1 as a lineage-specific oncogene in luminal type breast cancer

    Noritaka Yamaguchi, Emi Ito, Sakura Azuma, Reiko Honma, Yuka Yanagisawa, Akira Nishikawa, Mika Kawamura, Jun-ichi Imai, Kuniaki Tatsuta, Jun-ichiro Inoue, Kentaro Semba, Shinya Watanabe

    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS   365 ( 4 ) 711 - 717  2008.01

    　View Summary

    The forkhead transcription factor FoxA1 is thought to be involved in mammary tumorigenesis. However, the precise role of FoxA1 in breast cancer development is controversial. We examined expression of FoxA I in 35 human breast cancer cell lines and compared it with that of ErbB2, a marker of poor prognosis in breast cancer. We found that FoxA1 is expressed at high levels in all ErbB2-positive cell lines and a subset of ErbB2-negative cell lines. Down-regulation of FoxA1 by RNA interference significantly suppressed proliferation of ErbB2-negative and FoxA1-positive breast cancer cell lines. Down-regulation of FoxA1 also enhanced the toxic effect of Herceptin on ErbB2-positive cell lines through induction of apoptosis. Taken together with previous data that FoxA1 is a marker of luminal cells in mammary gland, our present results suggest that FoxA1 plays an important role as a lineage-specific oncogene in proliferation of cancer cells derived from mammary luminal cells. (c) 2007 Elsevier Inc. All rights reserved.

    DOI PubMed CiNii

  • Total synthesis and development of bioactive natural products

    Kuniaki Tatsuta

    Proceedings of the Japan Academy Series B: Physical and Biological Sciences   84 ( 4 ) 87 - 106  2008

    Book review, literature introduction, etc.  

    　View Summary

    The first total synthesis and development of a variety of bioactive natural products have been accomplished by using carbohydrates as a chiral source. In addition, practically useful intermediates have been created, analogs of natural products have been prepared, their structure-activity relationships studied, and the large-scale preparations of medicinally useful compounds established. The key target molecules have been the "Big Four" antibiotics (macrolides, aminoglycosides, β-lactams and tetracyclines), pyranonaphthoquinone antibiotics, glycosidase inhibitors, and a side-chain of cephem antibiotics. ©2008 The Japan Academy.

    DOI PubMed

  • Total Synthesis of Bioactive Products

    ETH seminer    2008

  • Learn from nature, and go beyond it - Medicinal developments

    ASMeW International Symposium    2008

  • The first total synthesis and structural determination of (+)-BE-52440A

    Kuniaki Tatsuta, Yoshikazu Suzuki, Tatsuya Toriumi, Yoshiaki Furuya, Seijiro Hosokawa

    TETRAHEDRON LETTERS   48 ( 45 ) 8018 - 8021  2007.11

    　View Summary

    The first total synthesis and structural determination of (+)-BE-52440A have been achieved by enantiodivergent synthesis. S-Bridging dimerization including S(N)2 epoxy-opening reaction of tetrasubstituted epoxide 2 with sodium sulfide has been achieved in excellent yield with high regioselectivity. The structure of (+)-BE-52440A was determined to be the dimer of kalafungin type pyranonaphthoquinone. (C) 2007 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis and structural determination of (+)-BE-52440A

    Kuniaki Tatsuta, Yoshikazu Suzuki, Tatsuya Toriumi, Yoshiaki Furuya, Seijiro Hosokawa

    TETRAHEDRON LETTERS   48 ( 45 ) 8018 - 8021  2007.11

    　View Summary

    The first total synthesis and structural determination of (+)-BE-52440A have been achieved by enantiodivergent synthesis. S-Bridging dimerization including S(N)2 epoxy-opening reaction of tetrasubstituted epoxide 2 with sodium sulfide has been achieved in excellent yield with high regioselectivity. The structure of (+)-BE-52440A was determined to be the dimer of kalafungin type pyranonaphthoquinone. (C) 2007 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis and structural determination of TMC-66

    Seijiro Hosokawa, Hitoshi Fumiyama, Hisato Fukuda, Tomohiro Fukuda, Masashi Seki, Kuniaki Tatsuta

    TETRAHEDRON LETTERS   48 ( 41 ) 7305 - 7308  2007.10

    　View Summary

    The first total synthesis and structural determination of TMC-66, an ECE inhibitor, was achieved in short steps by efficient construction and coupling of segments. The oxidative coupling with phenols attaching to electron-withdrawing groups was realized with a novel copper(II) reagent. (c) 2007 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis and structural determination of TMC-66

    Seijiro Hosokawa, Hitoshi Fumiyama, Hisato Fukuda, Tomohiro Fukuda, Masashi Seki, Kuniaki Tatsuta

    TETRAHEDRON LETTERS   48 ( 41 ) 7305 - 7308  2007.10

    　View Summary

    The first total synthesis and structural determination of TMC-66, an ECE inhibitor, was achieved in short steps by efficient construction and coupling of segments. The oxidative coupling with phenols attaching to electron-withdrawing groups was realized with a novel copper(II) reagent. (c) 2007 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis and structural determination of YCM1008A

    Kuniaki Tatsuta, Takahiro Yamaguchi, Yusuke Tsuda, Yumiko Yamaguchi, Nobutaka Hattori, Hiroshi Nagai, Seijiro Hosokawa

    TETRAHEDRON LETTERS   48 ( 24 ) 4187 - 4190  2007.06

    　View Summary

    The first total synthesis and structural determination of YCM1008A, a Ca2+ signaling inhibitor, have been achieved. The N-methoxy pyrano-pyridone moiety was synthesized by successive O- and N-conjugate additions with diketoamide 15. The absolute structure was determined to be (2R,3R,4S,8'R)-configuration. (c) 2007 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis and structural determination of YCM1008A

    Kuniaki Tatsuta, Takahiro Yamaguchi, Yusuke Tsuda, Yumiko Yamaguchi, Nobutaka Hattori, Hiroshi Nagai, Seijiro Hosokawa

    TETRAHEDRON LETTERS   48 ( 24 ) 4187 - 4190  2007.06

    　View Summary

    The first total synthesis and structural determination of YCM1008A, a Ca2+ signaling inhibitor, have been achieved. The N-methoxy pyrano-pyridone moiety was synthesized by successive O- and N-conjugate additions with diketoamide 15. The absolute structure was determined to be (2R,3R,4S,8'R)-configuration. (c) 2007 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis of vinaxanthone, a fungus metabolite possessing multiple bioactivities

    Kuniaki Tatsuta, Soko Kasai, Yuki Amano, Takahiro Yamaguchi, Masashi Seki, Seijiro Hosokawa

    Chemistry Letters   36 ( 1 ) 10 - 11  2007.01

    　View Summary

    Vinaxanthone (1) has been biomimetically synthesized from vanillin (2) through an intermolecular Diels-Alder cycloaddition between two molecules of the precursor 11. Copyright © 2007 The Chemical Society of Japan.

    DOI

  • The first total synthesis of vinaxanthone, a fungus metabolite possessing multiple bioactivities

    Kuniaki Tatsuta, Soko Kasai, Yuki Amano, Takahiro Yamaguchi, Masashi Seki, Seijiro Hosokawa

    Chemistry Letters   36 ( 1 ) 10 - 11  2007.01

    　View Summary

    Vinaxanthone (1) has been biomimetically synthesized from vanillin (2) through an intermolecular Diels-Alder cycloaddition between two molecules of the precursor 11. Copyright © 2007 The Chemical Society of Japan.

    DOI

  • Total synthesis of complicated natural products from simple carbohydrates

    233rd ACS National Meeting, Symposium in Memory of Prof. Aleksander Zamojski)    2007

  • 多様な天然生理活性物質の全合成と実践的展開

    北海道大学21COEシンポジウム    2007

  • The First Total Synthesis of Vinaxanthone, a Fungus Metabolite Possessing Multiple Bioactivities.

    Chem. Lett.   36 ( 1 ) 10 - 11  2007

    DOI CiNii

  • YCM1008A, a Novel Ca2+ -Signaling Inhibitor, Produced by Fusarium sp. YCM1008.

    F. Koizumi, N. Fukumitsu, J. Zhao, R. Chanklan, T. Miyakawa, S. Kawahara, S. Iwamoto, M. Suzuki, S. Kakita, E.S. Rahayu, S. Hosokawa, K. Tatsuta, M. Ichimura

    J. Antibiot.   60 ( 7 ) 455 - 458  2007

    DOI CiNii

  • Total Synthesis and Developments of Bioactive Natural Products

    A*STAR/野依フォーラム合同会議    2007

  • Total Synthesis and Developments of Bioactive Natural Products

    早稲田大学－上海交通大学合同シンポジウム    2007

  • 多様な天然生理活性物質の全合成と開発

    第18回万有仙台シンポジウム    2007

  • Total Synthesis of Furano-and Pyrano-naphthoquinone Antibiotics from Carbohydrates.

    234ｔｈ American Chemical Society National Meeting    2007

  • Total Synthesis and Developments of Bioactive Natural Products

    ワルシャワ大学セミナー    2007

  • Total Synthesis and Developments of Bioactive Natural Products

    ポーランドアカデミーシンポジウム    2007

  • Total synthesis of complicated natural products from simple carbohydrates

    233rd ACS National Meeting, Symposium in Memory of Prof. Aleksander Zamojski)    2007

  • The First Total Synthesis of Vinaxanthone, a Fungus Metabolite Possessing Multiple Bioactivities.

    Kuniaki Tatsuta, Soko Kasai, Yuki Amano, Takahiro Yamaguchi, Masashi Seki, Seijiro Hosokawa

    Chem. Lett.   36 ( 1 ) 10 - 11  2007

    DOI CiNii

  • YCM1008A, a Novel Ca2+ -Signaling Inhibitor, Produced by Fusarium sp. YCM1008.

    F. Koizumi, N. Fukumitsu, J. Zhao, R. Chanklan, T. Miyakawa, S. Kawahara, S. Iwamoto, M. Suzuki, S. Kakita, E.S. Rahayu, S. Hosokawa, K. Tatsuta, M. Ichimura

    J. Antibiot.   60 ( 7 ) 455 - 458  2007

    DOI CiNii

  • Total Synthesis and Developments of Bioactive Natural Products

    A*STAR/野依フォーラム合同会議    2007

  • Total Synthesis and Developments of Bioactive Natural Products

    早稲田大学－上海交通大学合同シンポジウム    2007

  • Total Synthesis of Furano-and Pyrano-naphthoquinone Antibiotics from Carbohydrates.

    234ｔｈ American Chemical Society National Meeting    2007

  • Total Synthesis and Developments of Bioactive Natural Products

    ワルシャワ大学セミナー    2007

  • Total Synthesis and Developments of Bioactive Natural Products

    ポーランドアカデミーシンポジウム    2007

  • Structure-activity relationships of xanthocillin derivatives as thrombopoietin receptor agonist

    Takahiro Yamaguchi, Yumi Miyake, Atsushi Miyamura, Norihisa Ishiwata, Kuniaki Tatsuta

    JOURNAL OF ANTIBIOTICS   59 ( 11 ) 729 - 734  2006.11

    Other  

    　View Summary

    Xanthocillin derivatives, which show thrombopoietin receptor agonist activity, were synthesized through our developed method. Bioassay data suggest the importance of alkene geometry, the presence of substituents at the benzene ring that support hydrophobic character, and the moderate size of the molecule. One of the two isonitrile group of the natural product appears to be dispensable.

    DOI

  • Structure-activity relationships of xanthocillin derivatives as thrombopoietin receptor agonist

    Takahiro Yamaguchi, Yumi Miyake, Atsushi Miyamura, Norihisa Ishiwata, Kuniaki Tatsuta

    JOURNAL OF ANTIBIOTICS   59 ( 11 ) 729 - 734  2006.11

    Other  

    　View Summary

    Xanthocillin derivatives, which show thrombopoietin receptor agonist activity, were synthesized through our developed method. Bioassay data suggest the importance of alkene geometry, the presence of substituents at the benzene ring that support hydrophobic character, and the moderate size of the molecule. One of the two isonitrile group of the natural product appears to be dispensable.

    DOI

  • The first total synthesis and structural determination of lagunamycin

    Seijiro Hosokawa, Shoichi Kuroda, Keisuke Imamura, Kuniaki Tatsuta

    TETRAHEDRON LETTERS   47 ( 35 ) 6183 - 6186  2006.08

    　View Summary

    Lagunamycin (1) has been synthesized by using our developed remote stereoinduction, Knorr condensation, periodinane oxidation, and diazonation. This enantioselective synthesis determined the absolute configuration of lagunamycin. Existence of rotational conformers was confirmed by NMR studies. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis and structural determination of lagunamycin

    Seijiro Hosokawa, Shoichi Kuroda, Keisuke Imamura, Kuniaki Tatsuta

    TETRAHEDRON LETTERS   47 ( 35 ) 6183 - 6186  2006.08

    　View Summary

    Lagunamycin (1) has been synthesized by using our developed remote stereoinduction, Knorr condensation, periodinane oxidation, and diazonation. This enantioselective synthesis determined the absolute configuration of lagunamycin. Existence of rotational conformers was confirmed by NMR studies. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis and structural determination of actinopyrone A

    Seijiro Hosokawa, Kazuya Yokota, Keisuke Imamura, Yasuaki Suzuki, Masataka Kawarasaki, Kuniaki Tatsuta

    TETRAHEDRON LETTERS   47 ( 30 ) 5415 - 5418  2006.07

    　View Summary

    Actinopyrone A (1) has been synthesized by using our developed remote stereoinduction, Kocienski olefination, Horner-Wadsworth-Emmons olefination, and reductive de-conjugation of the vinylpyrone. A concise method of O-methylation to obtain the gamma-pyrone has also been established. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • Total syntheses of bioactive natural products from carbohydrates

    Kuniaki Tatsuta, Seijiro Hosokawa

    SCIENCE AND TECHNOLOGY OF ADVANCED MATERIALS   7 ( 5 ) 397 - 410  2006.07

    Book review, literature introduction, etc.  

    　View Summary

    Total syntheses of bioactive natural products recently accomplished in our laboratories are described. They are classified by structures of target molecules and are focused on our original approach to their own structures. The target molecules include nanaomycin, kalafungin, BE-54238B, tetracycline, rosmarinecine, thienamycin, luminacines C-1 and C-2, tetrodecamycin, cochleamycin A, and tubelactomicin A, which have been synthesized as optically pure form from carbohydrates. (c) 2006 Published by NIMS and Elsevier Ltd.

    DOI CiNii

  • The first total synthesis and structural determination of actinopyrone A

    Seijiro Hosokawa, Kazuya Yokota, Keisuke Imamura, Yasuaki Suzuki, Masataka Kawarasaki, Kuniaki Tatsuta

    TETRAHEDRON LETTERS   47 ( 30 ) 5415 - 5418  2006.07

    　View Summary

    Actinopyrone A (1) has been synthesized by using our developed remote stereoinduction, Kocienski olefination, Horner-Wadsworth-Emmons olefination, and reductive de-conjugation of the vinylpyrone. A concise method of O-methylation to obtain the gamma-pyrone has also been established. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • Total syntheses of bioactive natural products from carbohydrates

    Kuniaki Tatsuta, Seijiro Hosokawa

    SCIENCE AND TECHNOLOGY OF ADVANCED MATERIALS   7 ( 5 ) 397 - 410  2006.07

    Book review, literature introduction, etc.  

    　View Summary

    Total syntheses of bioactive natural products recently accomplished in our laboratories are described. They are classified by structures of target molecules and are focused on our original approach to their own structures. The target molecules include nanaomycin, kalafungin, BE-54238B, tetracycline, rosmarinecine, thienamycin, luminacines C-1 and C-2, tetrodecamycin, cochleamycin A, and tubelactomicin A, which have been synthesized as optically pure form from carbohydrates. (c) 2006 Published by NIMS and Elsevier Ltd.

    DOI CiNii

  • The first total synthesis of a tetracyclic antibiotic, (-)-tetrodecamycin

    Kuniaki Tatsuta, Yasuaki Suzuki, Akiho Furuyama, Hiroshi Ikegami

    TETRAHEDRON LETTERS   47 ( 21 ) 3595 - 3598  2006.05

    　View Summary

    (-)-Tetrodecamycin (1) has been synthesized from optically active butenolide through stereoselective SmI2-mediated pinacol cyclization and newly developed deoxygenation. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis of a tetracyclic antibiotic, (-)-tetrodecamycin

    Kuniaki Tatsuta, Yasuaki Suzuki, Akiho Furuyama, Hiroshi Ikegami

    TETRAHEDRON LETTERS   47 ( 21 ) 3595 - 3598  2006.05

    　View Summary

    (-)-Tetrodecamycin (1) has been synthesized from optically active butenolide through stereoselective SmI2-mediated pinacol cyclization and newly developed deoxygenation. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • Total synthesis of an antitubercular lactone antibiotic, (+)-tubelactomicin A

    S Hosokawa, M Seki, H Fukuda, K Tatsuta

    TETRAHEDRON LETTERS   47 ( 14 ) 2439 - 2442  2006.04

    　View Summary

    (+)-Tubelactomicin A (1), an antitubercular lactone, has been synthesized from (S)-citronellol (2) and 2-deoxy-L-ribonolactone (18) through intramolecular Diels-Alder reaction, Suzuki-Miyaura coupling, and Shiina macrolactonization. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • Total synthesis of an antitubercular lactone antibiotic, (+)-tubelactomicin A

    S Hosokawa, M Seki, H Fukuda, K Tatsuta

    TETRAHEDRON LETTERS   47 ( 14 ) 2439 - 2442  2006.04

    　View Summary

    (+)-Tubelactomicin A (1), an antitubercular lactone, has been synthesized from (S)-citronellol (2) and 2-deoxy-L-ribonolactone (18) through intramolecular Diels-Alder reaction, Suzuki-Miyaura coupling, and Shiina macrolactonization. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • Practical Total Synthesis and Development of Bioactive Natural Products.

    Joint Symposium between Waseda University and National Taiwan University    2006

  • Anti-hypertensive effect and safety of long-term intake of a drink containing salmon peptide on high-normal blood pressure and mild hypertensive subjects

    Hiroyuki Enari, Yoshinori Takahashi, Motohiko Tada, Masataka Kawarasaki, Kuniaki Tatsuta, Ryuta Takeno, Osami Kajimoto

    Japanese Pharmacology and Therapeutics   34 ( 10 ) 1119 - 1135  2006

    　View Summary

    We established that salmon peptide which was digested from salmon muscle has angiotensin I-converting enzyme (ACE) inhibitory activity. Then, we examined the anti-hypertensive effect and safety of long-term intake of a drink containing salmon peptide on high-normal blood pressure and mild hypertensive subjects. This study was performed in a placebo-controlled, parallel, double-blind clinical test. One hundred and thirteen-subjects were divided into two groups before the study so that there were no statistical differences in the systolic blood pressure (SBP), diastolic blood pressure (DBP), age, sex and height. Test food group was given a drink (50mL/day) containing salmon peptide 1000mg, and placebo group was given a drink (50mL/day) which dose not contain salmon peptide once a day in the morning for 12 weeks. The results revealed that SBP in test food group was significantly reduced at 2, 4, 6 week after the intake and 2 week after the intake finished compared to the value before ingestion, and significant reduction in SBP was observed at 4 week after the intake in test food group compared to placebo group. Furthermore, in the analysis stratified mild hypertension pressure, SBP in test food group at 6 week after the intake were significantly decreased compared to the value before ingestion. In the analysis stratified high-normal blood pressure, SBP and DBP in test food group at 2 week after the intake were significantly decreased compared to placebo group. There were no clinical problems in the blood tests, urine tests and physical examinations. These results suggest that the drink containing salmon peptide is safe and useful for regulating the blood pressure in subjects with high-normal blood pressure and mild hypertension.

  • 天然物の全合成－華麗な戦略と方法－

    竜田邦明

    朝倉書店    2006

  • 生理活性物質の全合成とその実践的展開の重要性

    竜田邦明

    有合化   64 ( 5 ) 458 - 470  2006

    DOI CiNii

  • Total syntheses of polyketide-derived bioactive natural products

    Kuniaki Tatsuta, Seijiro Hosokawa

    CHEMICAL RECORD   6 ( 4 ) 217 - 233  2006

    Book review, literature introduction, etc.  

    　View Summary

    Recent progress of total syntheses in our laboratory has been described along with our background and methodologies. The target bioactive polyketides are classified into three categories according to their structures: (i) lactone-fused polycyclic compounds [(+)-cochleamycin A, (+)tubelactomicin A, and (-)-tetrodecamycin], (ii) aromatic compounds [H-tetracycline, H-BE-54238B, lymphostin, and (-)-laguna-mycin], and (iii) acyclic polyketides [xanthocillin X dimethylether, (+)-trichostatin D, and (+)-actinopyrone A]. Features of the total syntheses are described. Original methodologies have been developed and applied to construct the inherent structures of the target molecules. Most syntheses cited herein are the first total syntheses, and the absolute structures of the target molecules have been determined. (c) 2006 The Japan Chemical Journal Forum and Wiley Periodicals, Inc.

    DOI PubMed

  • Total Synthesis and Developments of Bioactive Natural Products

    Fiest International Conference on Advanced Organic Synthesis Directed toward the Ultimate Efficiency and Practicability    2006

  • 多様な天然生理活性物質の全合成

    第41回天然物化学談話会    2006

  • Total Synthesis and Developments of Bioactive Natural Products

    Cambridge-Oxford Symposium on Synthetic Organic Chemistry    2006

  • 天然に学び天然を超す−くすりを創る

    化学グランプリ講演会    2006

  • 多様な天然生理活性物質の全合成と実践的展開

    有機合成化学講演会    2006

  • Practical Total Synthesis and Development of Bioactive Natural Products.

    Joint Symposium between Waseda University and National Taiwan University    2006

  • Anti-hypertensive Effect and Safety of Long-term Intake of a Drink Containing Salmon Peptide on High-normal Blood Pressure and Mild Hypertensive Subjects.

    Hiroyuki Enari, Yoshinori Takahashi, Motohiko Tada, Masataka Kawarasaki, Kuniaki Tatsuta, Ryuta Takeno, Osami Kajimoto

    Jpn. Pharmacol. Ther.   34 ( 10 ) 1119 - 1135  2006

    　View Summary

    We established that salmon peptide which was digested from salmon muscle has angiotensin I-converting enzyme (ACE) inhibitory activity. Then, we examined the anti-hypertensive effect and safety of long-term intake of a drink containing salmon peptide on high-normal blood pressure and mild hypertensive subjects. This study was performed in a placebo-controlled, parallel, double-blind clinical test. One hundred and thirteen-subjects were divided into two groups before the study so that there were no statistical differences in the systolic blood pressure (SBP), diastolic blood pressure (DBP), age, sex and height. Test food group was given a drink (50mL/day) containing salmon peptide 1000mg, and placebo group was given a drink (50mL/day) which dose not contain salmon peptide once a day in the morning for 12 weeks. The results revealed that SBP in test food group was significantly reduced at 2, 4, 6 week after the intake and 2 week after the intake finished compared to the value before ingestion, and significant reduction in SBP was observed at 4 week after the intake in test food group compared to placebo group. Furthermore, in the analysis stratified mild hypertension pressure, SBP in test food group at 6 week after the intake were significantly decreased compared to the value before ingestion. In the analysis stratified high-normal blood pressure, SBP and DBP in test food group at 2 week after the intake were significantly decreased compared to placebo group. There were no clinical problems in the blood tests, urine tests and physical examinations. These results suggest that the drink containing salmon peptide is safe and useful for regulating the blood pressure in subjects with high-normal blood pressure and mild hypertension.

  • Total syntheses of polyketide-derived bioactive natural products

    Kuniaki Tatsuta, Seijiro Hosokawa

    CHEMICAL RECORD   6 ( 4 ) 217 - 233  2006

    Book review, literature introduction, etc.  

    　View Summary

    Recent progress of total syntheses in our laboratory has been described along with our background and methodologies. The target bioactive polyketides are classified into three categories according to their structures: (i) lactone-fused polycyclic compounds [(+)-cochleamycin A, (+)tubelactomicin A, and (-)-tetrodecamycin], (ii) aromatic compounds [H-tetracycline, H-BE-54238B, lymphostin, and (-)-laguna-mycin], and (iii) acyclic polyketides [xanthocillin X dimethylether, (+)-trichostatin D, and (+)-actinopyrone A]. Features of the total syntheses are described. Original methodologies have been developed and applied to construct the inherent structures of the target molecules. Most syntheses cited herein are the first total syntheses, and the absolute structures of the target molecules have been determined. (c) 2006 The Japan Chemical Journal Forum and Wiley Periodicals, Inc.

    DOI PubMed

  • Total Synthesis and Developments of Bioactive Natural Products

    Fiest International Conference on Advanced Organic Synthesis Directed toward the Ultimate Efficiency and Practicability    2006

  • Total Synthesis and Developments of Bioactive Natural Products

    Cambridge-Oxford Symposium on Synthetic Organic Chemistry    2006

  • Total synthesis of selected bioactive natural products: Illustration of strategy and design

    K Tatsuta, S Hosokawa

    CHEMICAL REVIEWS   105 ( 12 ) 4707 - 4729  2005.12

    Book review, literature introduction, etc.  

    DOI PubMed CiNii

  • Total synthesis of selected bioactive natural products: Illustration of strategy and design

    K Tatsuta, S Hosokawa

    CHEMICAL REVIEWS   105 ( 12 ) 4707 - 4729  2005.12

    Book review, literature introduction, etc.  

    DOI PubMed CiNii

  • The first stereoselective total synthesis of antiviral antibiotic, xanthocillin X dimethylether and its stereoisomer

    K Tatsuta, T Yamaguchi

    TETRAHEDRON LETTERS   46 ( 30 ) 5017 - 5020  2005.07

    　View Summary

    Xanthocillin X dimethylether (1) has been stereoselectively synthesized from the propiolic acid 6 through an oxidative rearrangement of the stannyl vinyl amide 27 to give the vinyl isocyanate 30 and a homocoupling of the stannyl N-formylenamine 31. (c) 2005 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first stereoselective total synthesis of antiviral antibiotic, xanthocillin X dimethylether and its stereoisomer

    K Tatsuta, T Yamaguchi

    TETRAHEDRON LETTERS   46 ( 30 ) 5017 - 5020  2005.07

    　View Summary

    Xanthocillin X dimethylether (1) has been stereoselectively synthesized from the propiolic acid 6 through an oxidative rearrangement of the stannyl vinyl amide 27 to give the vinyl isocyanate 30 and a homocoupling of the stannyl N-formylenamine 31. (c) 2005 Elsevier Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis of trichostatin D

    S Hosokawa, T Ogura, H Togashi, K Tatsuta

    TETRAHEDRON LETTERS   46 ( 2 ) 333 - 337  2005.01

    　View Summary

    Trichostatin D and 6-epi-trichostatin D have been stereoselectively svnthesized through a remote stereoinduction with a chiral vinylketene silyl N,O-acetal and glycosylation of hydroxymide under Mitsunobu conditions. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI

  • 多様な生理活性物質の全合成と開発

    有機合成化学協会シンポジウム    2005

  • 生理活性物質の実用的合成

    特定領域研究発表会    2005

  • 天然生理活性物質の全合成と開発

    北里大学特別講演会    2005

  • 天然生理活性物質の全合成と実践的展開

    日本化学会・高分子学会合同シンポジウム    2005

  • Practical Total Synthesis and Development of Bioactive Natural Products.

    Kyoto University 21COE Symposium    2005

  • Practical Total Synthesis and Development of Bioactive Natural Products.

    International Conference on Chemistry of Antibiotics and Bioactive Products    2005

  • 天然生理活性物質の全合成と実践的展開

    第49回日本薬学会    2005

  • Practical Total Synthesis and Development of Bioactive Natural Products.

    Waseda-day in Peking University    2005

  • Practical Total Synthesis and Development of Bioactive Natural Products.

    PACIFICHEM2005    2005

  • The first total synthesis of trichostatin D

    S Hosokawa, T Ogura, H Togashi, K Tatsuta

    TETRAHEDRON LETTERS   46 ( 2 ) 333 - 337  2005.01

    　View Summary

    Trichostatin D and 6-epi-trichostatin D have been stereoselectively svnthesized through a remote stereoinduction with a chiral vinylketene silyl N,O-acetal and glycosylation of hydroxymide under Mitsunobu conditions. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI

  • Practical Total Synthesis and Development of Bioactive Natural Products.

    Kyoto University 21COE Symposium    2005

  • Practical Total Synthesis and Development of Bioactive Natural Products.

    International Conference on Chemistry of Antibiotics and Bioactive Products    2005

  • Practical Total Synthesis and Development of Bioactive Natural Products.

    Waseda-day in Peking University    2005

  • Practical Total Synthesis and Development of Bioactive Natural Products.

    PACIFICHEM2005    2005

  • The first total synthesis of lymphostin

    K Tatsuta, K Imamura, S Itoh, S Kasai

    TETRAHEDRON LETTERS   45 ( 13 ) 2847 - 2850  2004.03

    　View Summary

    Lymphostin (1), a novel immunosuppressant, has been synthesized front tryptophan through six kinds of regioselectively oxidative reactions. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI

  • The first total synthesis of lymphostin

    K Tatsuta, K Imamura, S Itoh, S Kasai

    TETRAHEDRON LETTERS   45 ( 13 ) 2847 - 2850  2004.03

    　View Summary

    Lymphostin (1), a novel immunosuppressant, has been synthesized front tryptophan through six kinds of regioselectively oxidative reactions. (C) 2004 Elsevier Ltd. All rights reserved.

    DOI

  • 天然生理活性物質の全合成と実践的展開

    日本薬学会    2004

  • Practical Total Synthesis and Developments of Bioactive Natural Products.

    日韓合同化学シンポジウム    2004

  • Total Synthesis and Developments of Bioactive Natural Ploducts.

    健康推進教育国際会議    2004

  • 天然生理活性物質の全合成と実践的展開

    静岡県立大学シンポジゥム    2004

  • Practical Total Synthesis and Developments of Bioactive Natural Products.

    日中合同シンポジウム    2004

  • Practical Total Synthesis and Development of Bioactive Natural Products.

    21COE International Symposium    2004

  • The First Total Synthesis of a Pyranonaphthoquinone Antitumor, BE-54238B.

    TATSUTA K, HIRABAYASHI T, KOJIMA M, SUZUKI Y, OGURA T

    J. Antibiot.   57 ( 4 ) 291 - 297  2004

    DOI

  • Practical Total Synthesis and Developments of Bioactive Natural Products.

    日韓合同化学シンポジウム    2004

  • Total Synthesis and Developments of Bioactive Natural Ploducts.

    健康推進教育国際会議    2004

  • Practical Total Synthesis and Developments of Bioactive Natural Products.

    日中合同シンポジウム    2004

  • Practical Total Synthesis and Development of Bioactive Natural Products.

    21COE International Symposium    2004

  • The First Total Synthesis of a Pyranonaphthoquinone Antitumor, BE-54238B.

    J. Antibiot.   57 ( 4 ) 291 - 297  2004

    DOI

  • The first total synthesis of cochleamycin A and determination of the absolute structure [2]

    Kuniaki Tatsuta, Fumie Narazaki, Nobusuke Kashiki, Jun-Ichiro Yamamoto, Satoshi Nakano

    Journal of Antibiotics   56 ( 6 ) 584 - 590  2003.06

    Rapid communication, short report, research note, etc. (scientific journal)  

    DOI PubMed CiNii

  • Synthetic inhibitors of proline-rich ligand-mediated protein-protein interaction: Potent analogs of UCS15A

    C Oneyama, T Agatsuma, Y Kanda, H Nakano, SV Sharma, S Nakano, F Narazaki, K Tatsuta

    CHEMISTRY & BIOLOGY   10 ( 5 ) 443 - 451  2003.05

    　View Summary

    The proline-rich motif in proteins is known to function as a ligand sequence that binds to protein modules such as SH3, WW, and several other protein interaction domains. These proline-rich ligand-mediated protein-protein interactions (abbreviated PLPI) are important in many signaling pathways that are involved in various diseases. Our previous studies showed that UCS15A, produced by Streptomyces species, inhibited PLPI. Here we report on synthetic analogs of UCS15A that show more potent activity than UCS15A in inhibiting PLPI. A synthetic analog, compound 2c, blocked in vitro PLPI of Sam68-Fyn-SH3 as well as in vivo PLPI of Grb2-Sam68 and Grb2-Sos1. Activation of MEK was also inhibited by compound 2c. Unlike UCS15A, compound 2c was an order of magnitude less cytotoxic and did not cause morphological changes in treated cells.

    DOI

  • Isolation and synthesis of a new bioactive ellagic acid derivative from Combretum yunnanensis

    Y Asami, T Ogura, N Otake, T Nishimura, XS Yao, T Sakurai, H Nagasawa, S Sakuda, K Tatsuta

    JOURNAL OF NATURAL PRODUCTS   66 ( 5 ) 729 - 731  2003.05

    　View Summary

    A new ellagic acid derivative (1) was isolated from the branches of Combretum yunnanensis, and its structure was assigned as 4-(4"-O-acetyl-alpha-rhamnopyranosyl)ellagic acid by analysis of its spectral data. Total synthesis of 1 was achieved by the glycosylation of 3,3'-di-O-benzylellagic acid (5) with 4-O-acetyl-2,3-di-O-benzyl-L-rhamnose (4) as a key reaction, and the absolute configuration of I was determined. Compound 1 showed weak inhibitory activity against the growth of various tumor cells and inhibited HIV-1 protease.

    DOI PubMed CiNii

  • Synthetic inhibitors of proline-rich ligand-mediated protein-protein interaction: Potent analogs of UCS15A

    C Oneyama, T Agatsuma, Y Kanda, H Nakano, SV Sharma, S Nakano, F Narazaki, K Tatsuta

    CHEMISTRY & BIOLOGY   10 ( 5 ) 443 - 451  2003.05

    　View Summary

    The proline-rich motif in proteins is known to function as a ligand sequence that binds to protein modules such as SH3, WW, and several other protein interaction domains. These proline-rich ligand-mediated protein-protein interactions (abbreviated PLPI) are important in many signaling pathways that are involved in various diseases. Our previous studies showed that UCS15A, produced by Streptomyces species, inhibited PLPI. Here we report on synthetic analogs of UCS15A that show more potent activity than UCS15A in inhibiting PLPI. A synthetic analog, compound 2c, blocked in vitro PLPI of Sam68-Fyn-SH3 as well as in vivo PLPI of Grb2-Sam68 and Grb2-Sos1. Activation of MEK was also inhibited by compound 2c. Unlike UCS15A, compound 2c was an order of magnitude less cytotoxic and did not cause morphological changes in treated cells.

    DOI

  • Isolation and synthesis of a new bioactive ellagic acid derivative from Combretum yunnanensis

    Y Asami, T Ogura, N Otake, T Nishimura, XS Yao, T Sakurai, H Nagasawa, S Sakuda, K Tatsuta

    JOURNAL OF NATURAL PRODUCTS   66 ( 5 ) 729 - 731  2003.05

    　View Summary

    A new ellagic acid derivative (1) was isolated from the branches of Combretum yunnanensis, and its structure was assigned as 4-(4"-O-acetyl-alpha-rhamnopyranosyl)ellagic acid by analysis of its spectral data. Total synthesis of 1 was achieved by the glycosylation of 3,3'-di-O-benzylellagic acid (5) with 4-O-acetyl-2,3-di-O-benzyl-L-rhamnose (4) as a key reaction, and the absolute configuration of I was determined. Compound 1 showed weak inhibitory activity against the growth of various tumor cells and inhibited HIV-1 protease.

    DOI PubMed CiNii

  • Isolation and structural determination of spilacleosides A and B having a novel 1,3-dioxolan-4-one ring

    A Kameyama, Y Shibuya, H Kusuoku, Y Nishizawa, S Nakano, K Tatsuta

    TETRAHEDRON LETTERS   44 ( 13 ) 2737 - 2739  2003.03

    　View Summary

    As the first natural product incorporating 1,3-dioxotan-4-one in spiro structure, spilacleosides A and B were isolated from Ruscus aculeatus, and the absolute structures determined. (C) 2003 Elsevier Science Ltd. All rights reserved.

    DOI CiNii

  • Isolation and structural determination of spilacleosides A and B having a novel 1,3-dioxolan-4-one ring

    A Kameyama, Y Shibuya, H Kusuoku, Y Nishizawa, S Nakano, K Tatsuta

    TETRAHEDRON LETTERS   44 ( 13 ) 2737 - 2739  2003.03

    　View Summary

    As the first natural product incorporating 1,3-dioxotan-4-one in spiro structure, spilacleosides A and B were isolated from Ruscus aculeatus, and the absolute structures determined. (C) 2003 Elsevier Science Ltd. All rights reserved.

    DOI CiNii

  • 植物および微生物由来の抗癌物質と抗酸化物質の研究

    漢方医薬研究振興財団    2003

  • 天然生理活性物質の全合成と実践的展開

    21COE実践的ナノ化学国際シンポジウム    2003

  • 多様な生理活性物質の全合成と開発

    有機合成化学協会関東支部シンポジウム    2003

  • 多様な生理活性物質の実践的全合成と開発

    グリコクラスター公開シンポジウム    2003

  • 多様な生理活性物質の実践的全合成と開発

    日本プロセス化学会    2003

  • Total Synthesis and Developments of Bioactive Natural Products.

    スイス連邦工科大学    2003

  • Total Synthesis and Developments of Bioactive Natural Products.

    ポーランド科学アカデミー    2003

  • The First Total Synthesis of Cochleamycin A and Determination of the Absolute Structure.

    J. Antibiot.   56 ( 6 ) 584 - 590  2003

    DOI PubMed CiNii

  • Total Synthesis and Developments of Bioactive Natural Products.

    スイス連邦工科大学    2003

  • Total Synthesis and Developments of Bioactive Natural Products.

    ポーランド科学アカデミー    2003

  • 紫綬褒章

       2002

  • First Total Synthesis of (±)-Napyradiomycin Al.

    Chem. Lett.   ( 1 ) 14 - 15  2002

    DOI

  • Total Synthesis and Developments of Bioactive Compounds.

    日仏合同薬化学シンポジウム（フランス）    2002

  • Total Symthesis of Natural Products from Carbohydrates.

    アメリカ化学会    2002

  • Carbohydrate Synthons in Natural Products Chemistry Synthesis, Functionalization, and Applications

    アメリカ化学会    2002

  • My Favorite Organic Synthesis

    化学同人    2002

  • Total Synthesis of a Tetracyclic Anti-tumor, UCE6.

    TATSUTA K, INUKAI T, ITOH S, KAWARASAKI M, NAKANO Y

    J. Antibiot   55 ( 12 ) 1076 - 1080  2002

    DOI PubMed CiNii

  • First Total Synthesis of (±)-Napyradiomycin Al.

    Kuniaki Tatsuta, Yoshiki Tanaka, Masazumi Kojima, Hiroshi Ikegami

    Chem. Lett.   ( 1 ) 14 - 15  2002

    DOI

  • Total Synthesis and Developments of Bioactive Compounds.

    日仏合同薬化学シンポジウム（フランス）    2002

  • Total Symthesis of Natural Products from Carbohydrates.

    アメリカ化学会    2002

  • Carbohydrate Synthons in Natural Products Chemistry Synthesis, Functionalization, and Applications

    アメリカ化学会    2002

  • My Favorite Organic Synthesis

    化学同人    2002

  • Total Synthesis of a Tetracyclic Anti-tumor, UCE6.

    J. Antibiot   55 ( 12 ) 1076 - 1080  2002

    DOI PubMed CiNii

  • Design and synthesis of non-peptidic inhibitors for the Syk C-terminal SH2 domain based on structure-based in-silico screening

    T Niimi, M Orita, M Okazawa-Igarashi, H Sakashita, K Kikuchi, E Ball, A Ichikawa, Y Yamagiwa, S Sakamoto, A Tanaka, S Tsukamoto, S Fujita, K Tatsuta, Y Maeda, K Chikauchi

    JOURNAL OF MEDICINAL CHEMISTRY   44 ( 26 ) 4737 - 4740  2001.12

    　View Summary

    Structure-based in-silico screening was carried out for the Syk C-terminal SH2 domain. Fragments that could interact with the pY or pY+1 pockets were selected by our in-silico screening. After tethering two fragments bound to these pockets, we have designed and synthesized new compounds that show favorable interaction with the pY+3 pocket. One such compound, having a cyclohexylmalonic acid moiety identified as a novel potent phosphotyrosyl mimetic, exhibited an affinity comparable to that of the monophosphorylated ligand peptide.

    DOI PubMed CiNii

  • Design and synthesis of non-peptidic inhibitors for the Syk C-terminal SH2 domain based on structure-based in-silico screening

    T Niimi, M Orita, M Okazawa-Igarashi, H Sakashita, K Kikuchi, E Ball, A Ichikawa, Y Yamagiwa, S Sakamoto, A Tanaka, S Tsukamoto, S Fujita, K Tatsuta, Y Maeda, K Chikauchi

    JOURNAL OF MEDICINAL CHEMISTRY   44 ( 26 ) 4737 - 4740  2001.12

    　View Summary

    Structure-based in-silico screening was carried out for the Syk C-terminal SH2 domain. Fragments that could interact with the pY or pY+1 pockets were selected by our in-silico screening. After tethering two fragments bound to these pockets, we have designed and synthesized new compounds that show favorable interaction with the pY+3 pocket. One such compound, having a cyclohexylmalonic acid moiety identified as a novel potent phosphotyrosyl mimetic, exhibited an affinity comparable to that of the monophosphorylated ligand peptide.

    DOI PubMed CiNii

  • The first total synthesis and establishment of absolute structure of luminacins C1 and C2

    Kuniaki Tatsuta, Satoshi Nakano, Fumie Narazaki, Yusuke Nakamura

    Tetrahedron Letters   42 ( 43 ) 7625 - 7628  2001.10

    　View Summary

    Luminacins C1 and C2 (1 and 2), novel angiogenesis inhibitors, have been synthesized from a carbohydrate. The correlation of 1 and 2 confirms their structures to be different only at C1″ and establishes the relative and absolute configurations. © 2001 Elsevier Science Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis and establishment of absolute structure of luminacins C-1 and C-2

    K Tatsuta, S Nakano, F Narazaki, Y Nakamura

    TETRAHEDRON LETTERS   42 ( 43 ) 7625 - 7628  2001.10

    　View Summary

    Luminacins C-1 and C-2 (1 and 2), novel angiogenesis inhibitors, have been synthesized from a carbohydrate. The correlation of 1 and 2 confirms their structures to be different only at Cl " and establishes the relative and absolute configurations. (C) 2001 Elsevier Science Ltd. All rights reserved.

    DOI CiNii

  • 日本化学会賞

    日本化学会    2001

  • 多様な天然生理活性物質の実践的全合成と活性発現機構の解明

    日本化学会    2001

  • Glycoscience - Chemistry and Chemical Biology I-III.

    Springer - Verlag    2001

  • Total Syntheses of Useful Bioactive Compounds.

    Adv. Synth. Catal.    2001

  • Biomimetic total synthesis of quinolactacin B, TNF production inhibitor, and its analogs

    K Tatsuta, H Misawa, K Chikauchi

    JOURNAL OF ANTIBIOTICS   54 ( 1 ) 109 - 112  2001.01

    Rapid communication, short report, research note, etc. (scientific journal)  

  • Short and convergent synthesis of asterriquinone B1 and demethylasterriquinone B1

    K Tatsuta, H Mukai, K Mitsumoto

    JOURNAL OF ANTIBIOTICS   54 ( 1 ) 105 - 108  2001.01

    Rapid communication, short report, research note, etc. (scientific journal)  

  • The First Total Synthesis of a Macrocyclic Anti-protozoan, LL-Z1640-2.

    Chem. Lett.   ( 2 ) 172 - 173  2001

    DOI CiNii

  • Total Synthesis and Developments of Bioactive Compounds.

    国際化学療法会議（オランダ）    2001

  • Total Synthesis of Natural Products using Unsaturated Carbohydrates.

    アメリカ化学会年会    2001

  • Significance of Total Synthesis of Bioactive Compounds.

    Curr. Org. Chem.    2001

    DOI

  • Glycoscience - Chemistry and Chemical Biology I-III.

    Springer - Verlag    2001

  • Total Syntheses of Useful Bioactive Compounds.

    Adv. Synth. Catal.    2001

  • Biomimetic total synthesis of quinolactacin B, TNF production inhibitor, and its analogs

    K Tatsuta, H Misawa, K Chikauchi

    JOURNAL OF ANTIBIOTICS   54 ( 1 ) 109 - 112  2001.01

    Rapid communication, short report, research note, etc. (scientific journal)  

  • Short and convergent synthesis of asterriquinone B1 and demethylasterriquinone B1

    K Tatsuta, H Mukai, K Mitsumoto

    JOURNAL OF ANTIBIOTICS   54 ( 1 ) 105 - 108  2001.01

    Rapid communication, short report, research note, etc. (scientific journal)  

  • The First Total Synthesis of a Macrocyclic Anti-protozoan, LL-Z1640-2.

    Kuniaki Tatsuta, Satoko Takano, Toshimitsu Sato, Satoshi Nakano

    Chem. Lett.   ( 2 ) 172 - 173  2001

    DOI CiNii

  • Total Synthesis and Developments of Bioactive Compounds.

    国際化学療法会議（オランダ）    2001

  • Total Synthesis of Natural Products using Unsaturated Carbohydrates.

    アメリカ化学会年会    2001

  • Significance of total synthesis of bioactive compounds

    Kuniaki Tatsuta

    Current Organic Chemistry   5 ( 2 ) 207 - 231  2001

    Book review, literature introduction, etc.  

    　View Summary

    The first total synthesis and development of a variety of bioactive compounds have been accomplished mainly by using carbohydrates, if any, as chiral sources. The target molecules are macrolide antibiotics, aminoglycoside antibiotics, antifungal antibiotics, antitumor antibiotics, a side-chain of β-lactam antibiotics, enzyme inhibitors including glycosidase inhibitors, central nervous system - affecting products, nonsteroidal progesterone receptor ligands, mussel-attachment inhibitors and so on.

    DOI

  • Total Synthesis and Development of Medicinally Useful Natural Products.

    アメリカ化学会年会    2000

  • 糖類を用いる有用な生理活性物質の全合成と開発

    日本学術合成シンポジウム    2000

  • 有用な生理活性物質の全合成と開発―その意義と芸術性

    有機合成化学協会シンポジウム    2000

  • PF1163A and B, new antifungal antibiotics produced by Penicillium sp.II. Physico-chemical properties and structure elucidation.

    SASAKI T, NOSE H, HOSOYA A, YOSHIDA S, KAWAGUCHI M, WATANABE T, SHOMURA T, TAKANO S, TATSUTA K

    J. Antibiot.   53 ( 1 ) 38 - 44  2000

    DOI PubMed CiNii

  • The first total synthesis of Pyralomicin 1c.

    J. Antibiot.   53 ( 1 ) 88 - 91  2000

    DOI PubMed

  • 有用な生理活性物質の全合成と開発

    追手門学院創立50周年記念講演会    2000

  • 有用な生理活性物質の全合成と開発

    生理活性物質科学シンポジウム    2000

  • 有用な生理活性物質の全合成と開発

    北里大学    2000

  • 有用な生理活性物質の全合成と開発

    有機分子構築法に関するシンポジウム    2000

  • Total Synthesis of Natural Products Using Cycloaddition and Annulation.

    環太平洋国際化学会議    2000

  • Total Synthesis and Development of Useful Antibiotics.

    環太平洋国際化学会議    2000

  • Total Synthesis and Development of Useful Antibiotics.

    抗生物質国際化学会議（ポーランド）    2000

  • Total Synthesis and Development of Natural Products.

    アメリカ化学会年会    2000

  • Total Synthesis and Development of Bioactive Compounds.

    国際糖質シンポジウム（ハンブルグ）    2000

  • Total Synthesis and Development of Bioactive Compounds.

    アメリカ化学会年会    2000

  • 21世紀は「化学」から「化楽」へ

    有機合成化学協会誌   58;12  2000

  • 四大抗生物質の有機化学的全合成 ―挑戦と征服の軌跡―

    化学と工業   53;12  2000

  • 天然物の全合成におきた予想通りの奇跡

    有機合成化学協会誌   58;5  2000

  • 天然物の全合成ー今日, 明日, そして未来へ

    学会出版センター    2000

  • Novel Synthesis and Structural Elucidation of Quinolone Antibiotics PC-3 (SF2420B) and YM-30059.

    J. Antibiot.   53 ( 4 ) 418 - 421  2000

    DOI PubMed CiNii

  • Novel Synthesis of Natural Pseudo-aminosugars, (+)-Valienamine and (+)-Validamine.

    TATSUTA K, MUKAI H, TAKAHASHI M

    J. Antibiot.   53 ( 4 ) 430 - 435  2000

    DOI PubMed

  • The First Total Synthesis of Natural (-)-Tetracycline.

    TATSUTA K, YOSHIMOTO T, GUNJI H, OKADO Y, TAKAHASHI M

    Chem. Lett.   ( 6 ) 646 - 647  2000

    DOI

  • Novel Synthesis of (+)-4-Acetoxy-3-hydroxyethyl-2-azetidinone from Carbohydrate. Total Synthesis of (+)-Thienamycin.

    J. Antibiot.   53 ( 10 ) 1231 - 1234  2000

    DOI PubMed CiNii

  • Total Synthesis of Natural Products Using Cycloaddition and Annulation.

    環太平洋国際化学会議    2000

  • Total Synthesis and Development of Useful Antibiotics.

    環太平洋国際化学会議    2000

  • Total Synthesis and Development of Useful Antibiotics.

    抗生物質国際化学会議（ポーランド）    2000

  • Total Synthesis and Development of Natural Products.

    アメリカ化学会年会    2000

  • Total Synthesis and Development of Bioactive Compounds.

    国際糖質シンポジウム（ハンブルグ）    2000

  • Total Synthesis and Development of Bioactive Compounds.

    アメリカ化学会年会    2000

  • Novel Synthesis and Structural Elucidation of Quinolone Antibiotics PC-3 (SF2420B) and YM-30059.

    KUNIAKI TATSUTA, TAKUYA TAMURA

    J. Antibiot.   53 ( 4 ) 418 - 421  2000

    DOI PubMed CiNii

  • Novel synthesis of natural pseudo-aminosugars, (+)-valienamine and (+)-validamine

    Kuniaki Tatsuta, Hiroshi Mukai, Masaaki Takahashi

    Journal of Antibiotics   53 ( 4 ) 430 - 435  2000

    Rapid communication, short report, research note, etc. (scientific journal)  

    DOI PubMed

  • The First Total Synthesis of Natural (-)-Tetracycline.

    Chem. Lett.   ( 6 ) 646 - 647  2000

    DOI

  • Novel Synthesis of (+)-4-Acetoxy-3-hydroxyethyl-2-azetidinone from Carbohydrate. Total Synthesis of (+)-Thienamycin.

    KUNIAKI TATSUTA, MASAAKI TAKAHASHI, NOBORU TANAKA, KEN CHIKAUCHI

    J. Antibiot.   53 ( 10 ) 1231 - 1234  2000

    DOI PubMed CiNii

  • The first total synthesis of sideroxylonal B

    K Tatsuta, T Tamura, T Mase

    TETRAHEDRON LETTERS   40 ( 10 ) 1925 - 1928  1999.03

    　View Summary

    Sideroxylonal B (2c) has been synthesized through biomimetic cycloaddition of the o-quinone methide and the isopentenyl intermediates (5 and 6t), both of which were simultaneously derived from isopentenyl phloroglucinol precursor 4. (C) 1999 Elsevier Science Ltd. All rights reserved.

    DOI CiNii

  • The first total synthesis of pyralomicin 2c

    K Tatsuta, M Takahashi, N Tanaka

    TETRAHEDRON LETTERS   40 ( 10 ) 1929 - 1932  1999.03

    　View Summary

    Pyralomicin 2c (2) has been synthesized by N-glucosylation of the aglycone 16, which was prepared from the appropriately substituted pyrrole and benzoyl chloride (5 and 9). (C) 1999 Elsevier Science Ltd. All rights reserved.

    DOI CiNii

  • 有用な生理活性物質の全合成と開発

    有機合成化学協会北海道・東北支部総合講演会    1999

    DOI

  • 有用な生理活性物質の全合成と開発

    有機合成化学協会千葉シンポジウム    1999

    DOI

  • Total Synthesis and Development of Medicinally Useful Bioactive Compounds.

    抗生物質国際化学療法学会議    1999

  • 有用な生理活性物質の全合成と開発

    明治薬科大学特別講演会    1999

  • Total Synthesis and Development of Useful Natural Products.

    有機合成化学協会、東北有機合成コロキウム合同シンポジウム    1999

  • 海洋防汚物質シデロキシロナール類の全合成

    文部省科学研究費補助金特定領域研究発表会    1999

  • 有用な生理活性物質の全合成と開発

    文部省科学研究費補助金特定領域研究特別講演会    1999

  • 有用な生理活性物質の全合成と開発

    北里大学大学院特別講演会    1999

  • 合成するよろこびーより複雑な合成物への挑戦ー

    化学   54;12  1999

  • Synthesis of an N-Methyl-D-aspartate receptor antagonist, ES-242-5 and its analogs.

    TATSUTA K, NAGAI T, MASE T, YAMAZAKI T, TAMURA T

    J. Antibiot.   52 ( 4 ) 422 - 425  1999

    DOI PubMed

  • Absolute and atropisomeric structure of ES-242s, N-Methyl-D-aspartate receptor antagonists.

    TATSUTA K, NAGAI T, MASE T, TAMURA T, NAKAMURA H

    J. Antibiot.   52 ( 4 ) 433 - 436  1999

    DOI PubMed CiNii

  • The total synthesis and absolute structure of antifungal antibiotics (-)-PF1163A and B.

    TATSUTA K, TAKANO S, IKEDA Y, NAKANO S, MIYAZAKI S

    J. Antibiot.   52 ( 12 ) 1146 - 1151  1999

    DOI PubMed CiNii

  • The first total synthesis of a bioxanthracene (-)-ES-242-4, an N-methyl-D-aspartate receptor antagonist

    K Tatsuta, T Yamazaki, T Mase, T Yoshimoto

    TETRAHEDRON LETTERS   39 ( 13 ) 1771 - 1772  1998.03

    　View Summary

    Bioxanthracene (-)-ES-242-4 has been synthesized from oxidative dimerization of a naphthopyran which was derived from an alpha,beta-unsaturated lactone and methyl 2,4-dimethoxy-6-methylbenzoate through tandem Michael-Dieckmann reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.

    DOI CiNii

  • 平成９年度有機合成化学協会 協会賞受賞

       1998

  • The first total synthesis of (+/-)-terpestacin, HIV syncytium formation inhibitor

    K Tatsuta, N Masuda, H Nishida

    TETRAHEDRON LETTERS   39 ( 1-2 ) 83 - 86  1998.01

    　View Summary

    (+/-)-Terpestacin has been synthesized through C-alkylation of beta-keto lactone 9 with chain portion 12. These two compounds were derived from 2-cyclopenten-1-ylactic acid and E,E-farnesol, respectively. (C) 1997 Elsevier Science Ltd. All rights reserved.

    DOI CiNii

  • 有用な生理活性物質の全合成と開発

    東北大学大学院薬学研究科、特別講義    1998

    DOI

  • 有用な生理活性物質の全合成と開発

    有機合成化学協会東海支部総合講演会    1998

    DOI

  • Total Synthesis and Development of Useful Natural Products.

    ベルギー、ルーベン大学特別講演会    1998

  • 竜田フォーラム―有機化学工業の新時代―総まとめ

    日本化学会第６回技術開発フォーラム    1998

  • 早稲田大学理工学総合研究センター「生理活性・生体機能物質」シンポジウム―V（特別講演）「全合成と生理活性―その相補的意義」

    理工学総合研究センター    1998

  • The First Total Synthesis of Anti-HIV Terpestacin

    アメリカ、第19回国際糖質シンポジウム    1998

  • 有用な生理活性物質の全合成と開発

    理化学研究所、理研セミナー    1998

    DOI

  • 生理活性物質の全合成と活性―その相補的意義

    日本薬学会、第14回創薬セミナー    1998

  • 抗 HIV 活性を有するテルペスタシンの全合成

    文部省科学研究費補助金特定領域研究発表会    1998

  • Total Synthesis of Useful Natural Products

    International Sapporo Conference on Organic Synthesis and The 13th Nozaki Conference    1998

  • 有機合成化学協会賞受賞記念講演「有用な生理活性物質の全合成と開発」

    有機合成化学協会、第73回有機合成シンポジウム    1998

  • グリオザラーゼ I 阻害物質とその前駆体 KD16-U1 の全合成

    文部省科学研究費補助金特定領域研究発表会    1998

  • 神経系に作用するカロポロシド類の全合成と開発

    漢方医薬研究振興財団研究発表会    1998

  • Total Synthesis and Development of Glycosidase Inhibitor

    アメリカ化学会年会    1998

  • 有用な生理活性物質の全合成と開発

    理工学部ハイテクリサーチセンター    1998

    DOI

  • 竜田フォーラム―有機合成化学工業の新時代―知的機動力と芸術性

    日本化学会第4回技術開発フォーラム    1998

  • 有用な生理活性物質の全合成と開発

    有機合成化学協会誌   56;9  1998

    DOI

  • Total synthesis of a glyoxalase I inhibitor and its precursor, (-)-KD16-U1

    K Tatsuta, S Yasuda, N Araki, M Takahashi, Y Kamiya

    TETRAHEDRON LETTERS   39 ( 5-6 ) 401 - 402  1998.01

    　View Summary

    A glyoxalase I inhibitor and (-)-KD16-U1 have been synthesized from D-ribonic acid gamma-lactone through SnCl4-promoted cyclization of a phenylsulfonyl enol silyl ether and regioselective introduction of a hydroxymethyl group. (C) 1997 Elsevier Science Ltd. All rights reserved.

    DOI CiNii

  • Synthesis and biological evaluation of the analogs of bioxanthracenes ES-242s, N-methyl-D-aspartate antagonists.

    J. Antibiot.   51 ( 3 ) 383 - 386  1998

    DOI PubMed CiNii

  • The first total synthesis of natural (+)-terpestacin, Syncytium formation inhibitor.

    J. Antibiot.   51 ( 6 ) 602 - 606  1998

    DOI PubMed

  • 竜田フォーラムー有機化学工業の新時代

    日本化学会第6回技術開発フォーラム    1998

  • Total synthesis of progesterone receptor ligands, (-)-PF1092A, B and C

    K Tatsuta, S Yasuda, K Kurihara, K Tanabe, R Shinei, T Okonogi

    TETRAHEDRON LETTERS   38 ( 8 ) 1439 - 1442  1997.02

    　View Summary

    Microbial metabolites (-)-PF1092A, B and C belonging to an eremophilane sesquiterpene group are synthesized from (R)-5-hydroxymethyl-2(5H)-furanone through the SnCl4 promoted cyclization of an alpha-keto methyl sulfone and dimethyl acetal followed by a Stork annulation which gives the octalone core. (C) 1997 Elsevier Science Ltd.

    DOI CiNii

  • The first total synthesis of calbistrin A, a microbial product possessing multiple bioactivities

    K Tatsuta, M Itoh, R Hirama, N Araki, M Kitagawa

    TETRAHEDRON LETTERS   38 ( 4 ) 583 - 586  1997.01

    　View Summary

    The octahydronaphthopyranone moiety is synthesized from methyl alpha-D-mannopyranoside through the intramolecular Diels-Alder reaction, and the tetraenedicarboxylic acid moiety is from the enzymatically prepared anti-compound. Both moieties were coupled to accomplish the total synthesis of calbistrin A and to disclose its absolute structure. (C) 1997, Elsevier Science I,td. All rights reserved.

    DOI CiNii

  • The total synthesis of a glycosidase inhibitor,nagstatin.

    Bull. Chem. Soc. Jpn.   70 ( 2 ) 427 - 436  1997

    DOI

  • Total synthesis and molecular design of useful bioactive compounds.

    ドイツ、ハンブルグ大学特別講演会    1997

  • 四大抗生物質類の全合成

    日本抗生物質学術協議会    1997

  • 神経系に作用する微生物生産物の全合成

    脳機能に作用する活性成分と創薬シンポジウム    1997

  • 早稲田大学理工学総合研究センター「生理活性・生体機能物質」シンポジウム-IV(特別講演）

    早稲田大学理工学総合研究センター    1997

  • 有用な生理活性物質の全合成と開発

    日本薬学会年会    1997

  • 生理活性物質の全合成と分子設計

    岡山大学特別セミナー    1997

  • Total synthesis and chemical design of bioactive compounds.

    フランス、国立科学研究所天然物化学研究所講演会    1997

  • Total synthesis and molecular design of bioactive compounds.

    イギリス、ケンブリッジ大学特別講演会    1997

  • 有用な生理活性物質の全合成と分子設計

    北里大学薬学部特別講演会    1997

  • 立体特異的環化反応を鍵とする有用な生理活性物質の全合成

    文部省科学研究費補助金重点領域研究発表会    1997

  • 神経成長因子産生促進物質カルビストリンの全合成

    漢方医薬研究振興財団研究発表会    1997

  • 有用な生理活性物質の全合成と分子設計

    萬有福岡シンポジウム    1997

  • Total synthesis and molecular design of bioactive compounds.

    アジア化学会    1997

  • Total synthesis of natural products from unsaturated sugars.

    アメリカ化学会年会    1997

  • Total synthesis and molecular design of bioactive substances.

    台湾化学会年会    1997

  • Recent progress in total synthesis and development of natural products using carbohydrates.

    J. Synth. Org. Chem. Jpn.   55;11  1997

  • NK10958, a novel plant growth regulator produced by Steptomyces sp..

    J. Antibiot.   50 ( 3 ) 259 - 260  1997

    DOI

  • Epopromycins, nobel cell wall synthesis inhibitors of plant protoplast produced by Streptomyces sp. NK04000.

    J. Antibiot.   50 ( 3 ) 261 - 263  1997

    DOI CiNii

  • Total synthesis of MS-444, a myosin light chain kinasa inhibitor.

    J. Antibiot.   50 ( 3 ) 289 - 290  1997

  • Synthesis of (±)-PF1092A, B, and C, new nonsteroidal progesterone receptor.

    J. Antibiot.   50 ( 4 ) 360 - 362  1997

    DOI PubMed

  • Total synthesis of deacetyl-caloporoside, a novel inhibitor of the GABA(A) receptor ion channel

    K Tatsuta, S Yasuda

    TETRAHEDRON LETTERS   37 ( 14 ) 2453 - 2456  1996.04

    　View Summary

    The total synthesis of deacetyl-caloporoside (1) which contains a beta-D-mannopyranoside unit has been accomplished by coupling of the disaccharide-like segment derived from methyl alpha-D-mannopyranoside, with the hydroxyheptadecyl salicylic acid segment. The biological activity of 1 has also been evaluated. Copyright (C) 1996 Elsevier Science Ltd

    DOI CiNii

  • Total syntheses of bioactive substances

    Pfizer Medical Symposium    1996

  • Total synthesis and chemical design of useful glycosidase inhibitors

    The 16th Mona Symposium, Natural Products and Medicinal Chemistry 1996    1996

  • 天然物に学び，天然物を越す医薬品をつくる

    日本化学会「化学への招待」    1996

  • Tatal synthesis and chemical design of useful glycosidase inhibitors.

    Pure & Appl. Chem.   68;6  1996

    DOI

  • Enantiospecific total synthesis of tetracyclin.

    5th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Debrecen,Hungary    1996

  • Total syntheses of natural products affecting central nervous system.

    XVIII International Carbohydrate Symposium,Milano Italy    1996

  • Total synthesis and chemical design of useful glycosidase inhibitors.

    Second Euro Conference on Carbohydrate Mimics,Lago di Garda Italy    1996

    DOI

  • 生理活性物質の全合成と分子設計

    大阪大学薬学部高度推進特別講演会(特別講演）、大阪    1996

  • 全合成と生理活性-その相補的意義

    早稲田大学理工学総合研究センター「生理活性・生体機能物質」シンポジウム-III(特別講演）、東京    1996

  • 抗生物質カルビストリンの全合成研究

    第３８回天然有機化合物討論会、仙台    1996

  • 生理活性物質の全合成と開発

    第14回有機合成化学協会夏季大学(特別講演）、茅野    1996

  • 生理活性物質の合成にみる芸術性

    東京理科大学特別教室大学院セミナー(特別講演）、東京    1996

  • 天然物に学び天然物を越す一医薬品を作る

    日本化学会、化学への招待(特別講演）、東京    1996

  • GABA関連酵素阻害物質デアセチル-カロポシド類の全合成

    日本化学会第70回春季年会    1996

  • 抗生物質テトラサイクリンのエナンチオ特異的合成研究

    日本化学会第70回春季年会    1996

  • Synthesis and biological evaluation of caloporoside analogs.

    J. Antibiot.   49 ( 7 ) 713 - 715  1996

    DOI PubMed

  • Synthesis and glycosidase inhibitory activities of nagstatin triazole analogs.

    J. Antibiot.   49 ( 8 ) 836 - 838  1996

    DOI PubMed

  • NK154183A and B,antitumor substances produced by Streptomyces sp.

    TSUCHIYA K, KIMURA C, NISHIKAWA K, HARADA T, NISHIKIORI T, TSTSUTA K

    J.Antibiot.   49 ( 12 ) 1281 - 1283  1996

    DOI PubMed

  • TOTAL SYNTHESIS OF NAGSTATIN, AN N-ACETYL-BETA-D-GLUCOSAMINIDASE INHIBITOR

    K TATSUTA, S MIURA

    TETRAHEDRON LETTERS   36 ( 37 ) 6721 - 6724  1995.09

    　View Summary

    The first enantiospecific total synthesis of nagstatin has been accomplished through the regioselective introduction of an allyl group on the imidazole ring of the de-branched nagstatin precursor followed by conversion into the carboxymethyl group, and the stereospecific introduction of the acetamido group.

    DOI CiNii

  • TOTAL SYNTHESIS OF AN ACARICIDE, GUALAMYCIN

    K TATSUTA, M KITAGAWA

    TETRAHEDRON LETTERS   36 ( 37 ) 6717 - 6720  1995.09

    　View Summary

    The first enantiospecific total synthesis of gualamycin has been accomplished by coupling the thioglycoside of the amino-disaccharide portion with the strained di-O-benzylidene derivative of the pyrrolidine-aglycone.

    DOI

  • GUALAMYCIN, A NOVEL ACARICIDE PRODUCED BY STREPTOMYCES SP NK11687 .2. STRUCTURAL ELUCIDATION

    K TSUCHIYA, S KOBAYASHI, T KUROKAWA, T NAKAGAWA, N SHIMADA, H NAKAMURA, Y IITAKA, M KITAGAWA, K TATSUTA

    JOURNAL OF ANTIBIOTICS   48 ( 7 ) 630 - 634  1995.07

    　View Summary

    A novel acaricide, gualamycin was isolated from the culture broth of Streptomyces sp. NK 11687. The structure of gualamycin was determined to be (2R,3S,4S)-2-O-[4-O-(2-amino-2-deoxy-beta-D- gulopyranosyl)-alpha-D-galactopyranosyl]-2,3,4-trihydroxy-4-[(2S,3S,4S,5S)-3,4-dihydroxy-5-hydroxy-methylpyrrolidin-2-yl] butanoic acid by FAB-MS, H-1 and C-13 NMR, COSY, HMQC, HMBC, IR, X-ray crystallographic analyses and synthetic studies.

    DOI PubMed

  • Total synthesis and chemical design of useful glycosidase inhibitors

    Third IUPAC International Symposium on Bioorganic Chemistry    1995

  • Total synthesis and absolute structure of acaricidal gualamycin

    8th European Carbohydrate Symposium    1995

  • テトラサイクリン系抗生物質の不斉全合成

    第5回キラル分子の不斉合成シンポジウム    1995

  • 生理活性と創薬

    早稲田大学理工学総合研究センター テクノロジー系シンポジウム    1995

  • 殺ダニ物質グアラマイシンの全合成

    第37回天然有機化合物討論会    1995

  • 全合成と生理活性－その相補的意義と哲学

    「生理活性・生体機能シンポジウム-II」    1995

  • Application of highly stereocontrolled glycosidations employing 2,6-anhydro-2-thio sugars to the syntheses of erythromycin A and olivomycin A trisaccharide

    TOSHIMA K, NOZAKI Y, MUKAIYAMA S, TAMAI T, NAKATA M, TATSUTA K, KINOSHITA M

    J. Am. Chem. Soc.   117 ( 13 ) 3717 - 3727  1995

    DOI CiNii

  • Molecular design, chemical synthesis, and study of novel enediyne-sulfide systems related to the neocarzinostatin chromophore

    TOSHIMA K, OHTA K, OHASHI A, NAKAMURA T, NAKATA M, TATSUTA K, MATSUMURA S

    J. Am. Chem. Soc.   117 ( 17 ) 4822 - 4831  1995

    DOI CiNii

  • Syntheses and absolute structures of the disaccharide and aglycone of acaricidal gualamycin

    TATSUTA K, KITAGAWA M, HORIUCHI T, TSUCHIYA K, SHIMADA N

    J. Antibiot.   48 ( 7 ) 741 - 744  1995

    DOI PubMed CiNii

  • Characterization of an extracellular polysaccharide elaborated by TX-1, a new strain of Beijerinckia indica

    Biosci. Biotech. Biochem.   59 ( 9 ) 1628 - 1631  1995

    DOI CiNii

  • Total Synthesis and Development of Natural Products

    アメリカ化学会年会    1994

  • 他合計6件

     

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Internal Special Research Projects

  • 多様な天然生理活性物質の全合成と活性発現ユニットの解明

    2006  

    　View Summary

    神経再生作用を有する天然物ビナキサンソンの全合成ビナキサンソンは1991年に日本ロッシュの研究グループにより、Penicillium vinaceumの培養液より単離・構造決定された天然生理活性物質である。近年、大日本住友製薬のグループにより神経再生作用を有することが報告されており、脊髄損傷などに対する神経再生医薬品としての可能性が期待されている。本研究において、生合成過程を考慮した分子間Diels-Alder反応を鍵反応とするビナキサンソンの初の全合成を達成したので以下に概要を述べる。出発原料として入手容易なバニリンより4工程を経て臭化フェノール体を得た。臭化フェノール体をアクリロニトリルに対してMichael付加させ、ニトリル体を得た。これに対しFriedel-Crafts型反応を行い、位置選択的に環化反応を進行させ、目的とする環化体を得た。続いて環化体のカルボニル基を保護したのち、ハロゲン金属交換反応によりメチルエステル基を導入後、保護基を除去し、メチルエステル体へと導いた。メチルエステル体に対してアルファ位のヨウ素化を行った後、Heck反応を用いてビニルメチルケトンを導入し、鍵中間体へと導いた。次にこれに対して、ジ-tert-ブチルメチルフェノール存在下トルエンを溶媒として用い、封管中200℃で加熱することにより付加反応に続く芳香化反応を一挙に進行させ、ビナキサンソン前駆体を得た。このビナキサンソン前駆体に対して塩化アルミニウムを作用させてメチル基を除去した。得られた化合物はあらゆる性状において天然物と完全に一致したので、ビナキサンソンの初の全合成を完成し構造も確証した。本合成法はビナキサンソンの類縁体の合成にも応用可能であるので、今後、さらに体内動態の優れた化合物の合成を行う予定である。

  • 多様な天然生理活性物質の全合成と新規活性物質の創製

    2005  

    　View Summary

    　本研究は、まず、有用な天然生理活性物質の全合成を独自の合成法と戦略を展開して完成する。続いて、その手法を効果的に応用することによって種々の構造ユニットを合成し、構造－活性相関研究から活性発現機構を明らかにする。つぎに、特徴ある活性を構造ユニットごとに分離あるいは増強し、副作用の少ない新薬のリード化合物を創製し工業的合成法も開発することを目的とする。この過程において新しい活性の発見と展開も期待できる。　研究対象物質は、多様な生理活性や絶対構造が未決定のために展開が遅れているが、新規医薬品としての開発が期待されている下記の７種類の天然物である。　合成研究の結果、それぞれの天然物について今年度の所期の目標を達成した。１）免疫抑制作用と制がん作用を示すlymphostinの最初の全合成を完成し、さらに構造－活性相関研究の結果、新たに制がん作用を有する構造ユニットを見いだした。２）制がん作用を有するBE-54238Bの最初の全合成を完成し、絶対構造を決定した。また、中間体のnanaomycin類縁体が強い抗真菌作用を示すことを見いだした。３）抗ウイルス作用とTPO受容体アゴニスト活性を示すxanthocillin X dimethyletherの最初の立体選択的全合成を完成し立体配置を確定した。また、構造－活性相関研究の結果、活性発現の最小ユニットを見いだした。４）制がん作用を有するtrichostatin類の最初の全合成を完成すると共にtrichostatin Aの絶対構造も決定した。５）結核菌に強い活性を示すtubelactomicin Aの全合成を完成した。６）養殖魚の病原菌に有効な活性を有するtetrodecamycinの最初の全合成を完成し絶対構造を確定した。７）中枢神経に関与するGABAの拮抗物質であり、抗菌活性を示すxenovuleneの全合成に必要な構造ユニットの合成を行った。

  • 生理活性物質創製のための新規有機合成反応の開発

    1999   清水　功雄, 吉本　卓司, 山本　明夫

    　View Summary

    　１）HIV活性を示すテルペスタシンの全合成と絶対構造決定：テルペスタシンは、二環性5-15員構造を有しているが、D-ガラクトースを不斉炭素源として5員環部分を合成した後、15員環部分を効率よく結合させ、立体配置と置換基を整備して全合成を完成させた。２）N-メチルD-アスパルタート受容体拮抗物質ES-242類の全合成、絶対構造決定および活性発現機構解明：L-ラムノースを原料にし連続するMichael-Dieckmann反応を経てナフトピラン誘導体を合成した後、酸化的カップリングによる二量化を経てES-242-4およびその類縁体を全合成した。軸不斉によるすべてのジアステレオマーの絶対構造を明らかにすると共に、構造―活性相関研究に基づいて二つの水酸基の距離が活性発現の主要因であることを明らかにした。３）海洋防汚物質シデロキシロナール類の全合成と相対構造決定：2-フェニルベンゾピラン骨格をもち、船底や漁網への貝殻の付着を阻害するシデロキシロナール類を生合成類似の反応、すなわち同一系内で生成させたオルトキノンメチドとオレフィンから［4+2]環状付加反応を用いて合成した。従来、生合成過程は知られていたが、生合成類似の有機化学的合成は報告されていなかった。合成後、2,3:3,4-トランス、トランス体が天然からもシデロキシロナールCとして単離され、すべての構造を決定した。４）光学活性なカルバサイクル類の新規合成法の開発：カルバサイクル類の一般的合成を開発し、代表的な天然物を全合成して、その有用性と汎用性を例証した。その鍵反応は、メチルフェニルスルホンをラクトンに反応して得られるフラノース体をシリル化により一段階で開環し、続いて分子内アルドール縮合によって閉環し、シクロヘキセノン体を得る点にある。本方法論を活用して、抗真菌抗生物質ピラロマイシン類の全合成およびグリコシダーゼ阻害物質(+)-バリエナミンおよびバリダミンの全合成を完成した。

  • 有用なグリコシダーゼ阻害物質の合成と開発

    1997  

    　View Summary

    近年、グリコシダーゼやグリコシルトランスフェラーゼが生合成や分解を通して糖質の係わる生体機能を支配していることが明らかにされてきた。このことは、これら酵素の阻害剤が生体機能の解明に役立つばかりではなく、これら酵素の異常によって引き起こされる疾病に対する治療薬になる可能性を示唆している。今回、本研究者らは、N - アセチル -β- D - グルコサミニダーゼの強い阻害物質であり、糖尿病薬あるいは抗エイズ薬として期待されているナグスタチンの全合成を初めて完成すると共に工業的合成法を確立した。すなわち、L-リボフラノース誘導体にイミダゾールを反応させた後、分子内求核反応を経て、イミダゾール環の縮環した二環性アザ糖質を合成した。これに、側鎖のアセチル部分を位置選択的に導入して、天然型ナグスタチンを得た。さらに、L-キシロースなどを出発原料にして、ナグスタチンの立体配置および置換基の異なる種々の類縁体を合成し、それらの構造活性ー相関研究を行った。その結果、他のグリコシダーゼ にも特異的に阻害活性を示す化合物が得られることを見いだした。終局的に、それらがそれぞれの基質と拮抗的に作用して酵素阻害活性を示すことを明かにし、理論的にすべてのグリコシダーゼ（糖分解酵素）の阻害物質を合成できることを例証した。　一方、殺ダニ物質グアラマイシンを、D -グルコサミン、D - グルコースおよび L - グルカールなどを出発原料にして全合成することに初めて成功した。しかし、天然のグアラマイシンは、比較的不安定であり、失活するので、安定で且つ強力な殺ダニ活性をもつ類縁体の合成を試みた。その結果、ピロリジン部分をメチル化することによって目的が達成できることを見いだした。また、その活性発現が糖分解酵素の一種であるマルターゼの阻害活性によることを明かにした。　したがって、本研究は、有用なグリコシダーゼの阻害物質の合成と開発を基盤として、有用な医薬品の開発を含め、有機工業化学のみならず有機合成化学的にも意義をもつものである。研究成果の発表1) １９９７年４月：Kuniaki Tatsuta, Manabu Itoh, Ryusuke Hirama, Nobuyuki Ar aki and Masayuki Kitagawa： The first total synthesis of calbistrin A a microbial product possessing multiple bioactivities. Tetrahedron Lett., 38 (4), 583-586 (1997).　2) １９９７年４月：Kuniaki Tatsuta, Shohei Yasuda, Ken-ichi Kurihara, Kiyoshi Tanabe, Rie Shinei and Tsuneo Okonogi： Total synthesis of progesterone receptor ligands, (-)-PF1092A, B and C. Tetrahedron Lett., 38 (8), 1439 - 1442 (1997).　　3) １９９７年４月：Kuniaki Tatsuta, Shozo Miura and Hiroki Gunji： The total synthesis of a glycosidase inhibitor, nagstatin. Bull. Chem. Soc. Jpn., 70 (4), 427 - 436 (1997).4) １９９７年１１月：Kuniaki Tatsuta： Recent progress in total synthesis and development of natural products using carbohydrates. J. Synth. Org. Chem. Jpn., 55 (11), 970 - 981 (1997).5) １９９７年１月：Kuniaki Tatsuta, Nobuyuki Masuda and Hidemitsu Nishida： The first total synthesis of (±)-terpestacin, HIV syncytium formation inhibitor. Tetrahedron Lett., 39 (1), 83 - 86 (1998).　6) １９９７年２月：Kuniaki Tatsuta, Shohei Yasuda, Nobuyuki Araki, Masaaki Takahashi and Yuko Kamiya： Total synthesis of a glyoxalase I inhibitor and its precursor, (-)-KD16-U1. Tetrahedron Lett., 39 (2), 401 - 402 (1998).