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Catalytic asymmetric total synthesis of caprazamycin, an anti-tuberculosis antibiotic

Research Project

Project/Area Number 23590037
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionMicrobial Chemistry Research Foundation

Principal Investigator

WATANABE Takumi  公益財団法人微生物化学研究会, 微生物化学研究所 有機合成研究部, 主席研究員 (80270544)

Co-Investigator(Kenkyū-buntansha) SHIBASAKI Masakatsu  (公財)微生物化学研究会, 微生物化学研 究所, 所長 (30112767)
Co-Investigator(Renkei-kenkyūsha) ABE Hikaru  (公財)微生物化学研究会, 微生物化学研 究所 有機合成研究部, 研究員 (10462269)
Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2011: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords全合成 / 天然有機化合物 / 触媒的不斉反応 / 抗結核剤 / 有機化学 / 抗結核薬
Research Abstract

A study on catalytic asymmetric total synthesis of caprazamycin, an anti-TB antibiotic, was conducted. The synthesis would be applied to structure-activity relationship study on the related compounds.
To install the correct stereochemistries embedded in the structure of caprazamycin, catalytic enantioselective nitroaldol- and thioamide aldol reactions that have been recently reported from the laboratory, newly developed catalytic asymmetric alcoholysis of 3-methylglutaric anhydride, and diastereoselective isocyanoacetate aldol reaction were utilized. During course of the study, catalytic asymmetric total synthesis of caprazol was accomplished.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (23 results)

All 2014 2013 2012 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results) Presentation (18 results) (of which Invited: 1 results) Remarks (2 results)

  • [Journal Article] Catalytic asymmetric total synthesis of (+)-caprazol2014

    • Author(s)
      Gopinath, P., Wang, L., Abe, H., Ravi, G., Masuda, T., Watanabe, T., Shibasaki, M.
    • Journal Title

      Org. Lett

      Volume: 16 Issue: 12 Pages: 3364-3367

    • DOI

      10.1021/ol501397b

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Studies on Catalytic Enantioselective Total Synthesis of Caprazamycin B : Construction of the Western Zone2012

    • Author(s)
      Gopinath, P., Watanabe, T. & Shibasaki M
    • Journal Title

      J. Org. Chem.

      Volume: 77 Issue: 20 Pages: 9260-9267

    • DOI

      10.1021/jo301803h

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Catalytic eiantioselective desymmetrization of meso-glutaric anhydrides using a stable Ni_2-Schiff base catalys2012

    • Author(s)
      Gopinath, P., Watanabe, T., Shibasaki, M.
    • Journal Title

      Org.Lett.

      Volume: 14 Issue: 5 Pages: 1358-1361

    • DOI

      10.1021/ol3002078

    • Related Report
      2013 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Presentation]2014

    • Author(s)
      Gopinath Purushothaman,Ravi Gandamala,舛田岳史,渡辺匠,柴﨑正勝
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学・黒髪キャンパス(熊本市)
    • Year and Date
      2014-03-28
    • Related Report
      2013 Final Research Report
  • [Presentation] Study on catalytic asymmetric total synthesis of caprazamycin B2013

    • Author(s)
      Takumi Watanabe, Purushothaman Gopinath, Takashi Masuda, Gandamala Ravi, Masakatsu Shibasaki
    • Organizer
      18th European symposium on organic chemistry
    • Place of Presentation
      Palais du Pharo (Marseille,France)
    • Year and Date
      2013-07-08
    • Related Report
      2013 Final Research Report
  • [Presentation] Studies on catalytic enantioselective total synthesis of caprazamycin B2013

    • Author(s)
      Gopinath Purushothaman,舛田岳史,渡辺匠,柴﨑正勝
    • Organizer
      第103回有機合成シンポジウム
    • Place of Presentation
      慶應義塾大学薬学部・芝共立キャンパス(東京都港区)
    • Year and Date
      2013-06-06
    • Related Report
      2013 Final Research Report
  • [Presentation] Studies on catalytic enantioselective total synthesis of caprazamycin B2013

    • Author(s)
      Gopinath Purushothaman,舛田岳史,渡辺匠,柴﨑正勝
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜(横浜市)
    • Year and Date
      2013-03-30
    • Related Report
      2013 Final Research Report
  • [Presentation] 抗結核活性を有する核酸系抗生物質caprazamycinBの触媒的不斉合成研究2012

    • Author(s)
      プルショタマンゴピナス,渡辺匠,柴﨑正勝
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2012-11-05
    • Related Report
      2013 Final Research Report
  • [Presentation] Study on catalytic asymmetric total synthesis of caprazamycin B2012

    • Author(s)
      Takumi Watanabe, Purushothaman Gopinath, Takashi Masuda, Masakatsu Shibasaki
    • Organizer
      第6回武田科学振興財団薬科学シンポジウム
    • Place of Presentation
      武田薬品工業㈱研修所(吹田市)
    • Year and Date
      2012-09-13
    • Related Report
      2013 Final Research Report
  • [Presentation] Study on catalytic asymmetric total synthesis of caprazamycin B2012

    • Author(s)
      T akumi Watanabe, Purushothaman Gopinath, Masakatsu Shibasaki
    • Organizer
      19th Intrnational conference on organic synthesis
    • Place of Presentation
      Melbourne Convention & Exhibition Centre (Melbourne,Australia)
    • Year and Date
      2012-07-04
    • Related Report
      2013 Final Research Report
  • [Presentation] Caprazamycin Bの触媒的不斉合成研究:1,2-syn-アミノアルコール部位の立体選択的構築2012

    • Author(s)
      渡辺匠、プルショタマンゴピナス、柴﨑正勝
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学・札幌キャンパス(札幌市)
    • Year and Date
      2012-03-30
    • Related Report
      2013 Final Research Report
  • [Presentation] Progress towards the catalytic enantioselective total synthesis of caprazamycin B : Synthesis of the western zone2012

    • Author(s)
      Gopinath Purushothaman,渡辺匠,柴﨑正勝
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学・札幌キャンパス(札幌市)
    • Year and Date
      2012-03-29
    • Related Report
      2013 Final Research Report
  • [Presentation] Caprazamycin Bの触媒的不斉合成研究:1,2-syn-アミノアルコール部位の立体選択的構築2012

    • Author(s)
      渡辺 匠、プルショタマン ゴピナス、柴崎正勝
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌(北海道大学札幌キャンパス)
    • Related Report
      2011 Research-status Report
  • [Presentation] Progress towards the catalytic enantioselective total synthesis of caprazamycin B: Synthesis of the western zone.2012

    • Author(s)
      Gopinath Purushothaman, 渡辺 匠、柴崎正勝
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌(北海道大学札幌キャンパス)
    • Related Report
      2011 Research-status Report
  • [Presentation] Study on Catalytic Asymmetric Total Synthesis of Caprazamycin B

    • Author(s)
      Takumi Watanabe, Purushothaman Gopinath, Takashi Masuda, Gandamala Ravi, Masakatsu Shibasaki
    • Organizer
      18th European Symposium on Organic Chemistry
    • Place of Presentation
      Marseille (Palais du Pharo), France
    • Related Report
      2013 Annual Research Report
  • [Presentation] Caprazamycin Bの触媒的不斉全合成研究

    • Author(s)
      Gopinath Purushothaman, Ravi Gandamala,舛田岳史、渡辺 匠、柴﨑正勝
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本市(熊本大学・黒髪キャンパス)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Study on catalytic asymmetric total synthesis of caprazamycin B

    • Author(s)
      Takumi Watanabe, Purushothaman Gopinath, Masakatsu Shibasaki
    • Organizer
      19th International Conference on Organic Synthesis
    • Place of Presentation
      オーストラリア・メルボルン(Melbourne Convention & Exhibition Centre)
    • Related Report
      2012 Research-status Report
  • [Presentation] Study on catalytic asymmetric total synthesis of caprazamycin B

    • Author(s)
      Takumi Watanabe, Purushothaman Gopinath, Takashi Masuda, Masakatsu Shibasaki
    • Organizer
      第6回武田科学技術振興財団薬科学シンポジウム
    • Place of Presentation
      大阪・吹田市(武田薬品工業(株)研修所)
    • Related Report
      2012 Research-status Report
  • [Presentation] 医薬関連化合物の触媒的不斉合成研究

    • Author(s)
      渡辺 匠
    • Organizer
      東京大学医科学研究所-微生物化学研究所 連携研究キックオフシンポジウム
    • Place of Presentation
      東京・東京大学医科学研究所
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 抗結核活性を有する核酸系抗生物質Caprazamycin Bの触媒的不斉合成研究

    • Author(s)
      プルショタマンゴピナス,渡辺匠,柴﨑正勝
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      東京都江戸川区(タワーホール船堀)
    • Related Report
      2012 Research-status Report
  • [Presentation] Progress towards the catalytic enantioselective total synthesis of Caprazamycin B: Synthesis of the western zone

    • Author(s)
      プルショタマンゴピナス,渡辺匠,柴﨑正勝
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜(パシフィコ横浜)
    • Related Report
      2012 Research-status Report
  • [Remarks]

    • URL

      http://www.bikaken.or.jp/

    • Related Report
      2013 Final Research Report
  • [Remarks] The Shibasaki Lab.

    • URL

      http://www.bikaken.or.jp/research/group/shibasaki/shibasaki-lab/index.html

    • Related Report
      2013 Annual Research Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

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