• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Synthetic Study of Gymnocin-A, a Cytotoxic Marine Polycyclic Ether

Research Project

Project/Area Number 24590033
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionMeijo University

Principal Investigator

MORI Yuji  名城大学, 薬学部, 教授 (40121511)

Co-Investigator(Renkei-kenkyūsha) SAKAI Takeo  名城大学, 薬学部, 助教 (90583873)
Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsポリ環状エーテル / 収束的合成 / 赤潮毒 / ギムノシン / 全合成 / 渦鞭毛藻 / Karenia mikimotoi / 収束型合成
Outline of Final Research Achievements

Gymnocin-A was isolated from a culture of red-tide dinoflagellate Karenia mikimotoi. The structure of gymnocin-A is characterized by a stunning array of 14 contiguous ether rings and shows cyctotoxic activity against P388 mouse leukemia cells.
The synthetic studies toward the total synthesis of gymnocin-A have been carried out. In this study, synthesis of the three ABC-, FGH-, and KLMN-ring fragments was achieved in a convergent manner. The key feature of this approach is carbon-carbon bond formation by an oxiranyl anion coupling, which was followed by intramolecular Williamson ether synthesis and the reductive etherification of an cyclic acetal.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (27 results)

All 2015 2014 2013 2012 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Acknowledgement Compliant: 1 results) Presentation (18 results) (of which Invited: 3 results) Remarks (3 results)

  • [Journal Article] Synthesis of the KLMN Fragment of Gymnocin-A Using Oxiranyl Anion Convergent Methodology2014

    • Author(s)
      坂井健男、浅野晴日、古川恭子、大島里恵、森裕二
    • Journal Title

      Org. Lett

      Volume: 16巻 Issue: 8 Pages: 2268-2271

    • DOI

      10.1021/ol500788c

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic Study of Gymnocin-A: Synthesis of the ABC Ring Fragment2014

    • Author(s)
      Takeo Sakai, Shingo Matsushita, Shogo Arakawa, Atsuko Kawai, Yuji Mori
    • Journal Title

      Tetrahedron Letters

      Volume: 48 Issue: 48 Pages: 6557-6560

    • DOI

      10.1016/j.tetlet.2014.10.014

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of fused tetrahydropyrans by hydroalkoxylation of δ-hydroxy allenes2013

    • Author(s)
      Yumie Suzuki, Ayano Kuwabara, Yasuhiro Koizumi, Yuji Mori
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 43 Pages: 9086-9095

    • DOI

      10.1016/j.tet.2013.08.026

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Functionalized Tetracyanocyclopentadienides from Tetracyanothiophene and Sulfones2013

    • Author(s)
      坂井健男、瀬尾昭平、松岡純平、森裕二
    • Journal Title

      J. Org. Chem

      Volume: 78巻 Issue: 21 Pages: 10978-10985

    • DOI

      10.1021/jo401946j

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Mechanism of the Regio- and Diastereoselective Ring Expansion Reaction Using Trimethylsilyldiazomethane2012

    • Author(s)
      坂井健男、伊藤聡志、古田大貴、河原佑樹、森裕二
    • Journal Title

      Org. Lett

      Volume: 14巻 Issue: 17 Pages: 4564-4567

    • DOI

      10.1021/ol302032w

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Divergent Synthesis of Trans-Fused Polycyclic Ethers by a Convergent Oxiranyl Anion Strategy2012

    • Author(s)
      Takeo Sakai, Ai Sugimoto, Hiroki Tatematsu, Yuji Mori
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 77 Issue: 24 Pages: 11177-11191

    • DOI

      10.1021/jo302267f

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Gymnocin-BのBCD環システムの合成2015

    • Author(s)
      河合敦子、石橋廉司、坂井健男、森 裕二
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] Gymnocin-BのGHI環フラグメントの合成研究2015

    • Author(s)
      加藤翔大、波多野良紀、坂井健男、森 裕二
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] Gymnocin-AのFGHIJKLMN環フラグメントの合成2015

    • Author(s)
      坂井健男、徳升昇大、谷本美樹、吉田達司、森 裕二
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] オキシラニルアニオン法を用いたGymnocin-Aの収束的全合成研究2014

    • Author(s)
      坂井 健男、松下真吾、徳升晃大、河合敦子、荒川正悟、吉田達司、谷本美樹、森 裕二
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      仙台市
    • Year and Date
      2014-11-10
    • Related Report
      2014 Annual Research Report
  • [Presentation] Gymnocin-Aの全合成研究―ABCフラグメントの合成―2014

    • Author(s)
      荒川正悟、松下真吾、河合敦子、坂井健男、森 裕二
    • Organizer
      第60回日本薬学会東海支部大会
    • Place of Presentation
      鈴鹿市
    • Year and Date
      2014-07-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] Gymnocin-Aの全合成研究―FGHフラグメントの合成―2014

    • Author(s)
      吉田達司、森 巧一、徳升昇大、坂井健男、森 裕二
    • Organizer
      第60回日本薬学会東海支部大会
    • Place of Presentation
      鈴鹿市
    • Year and Date
      2014-07-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] Total Synthesis of Gambierol, a Polycyclic Ether Marine Toxin

    • Author(s)
      Yuji Mori
    • Organizer
      28th Sympojium on Natural Products
    • Place of Presentation
      Taipei, Taiwan
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Gymnocin-AのF/K環立体異性体の反転研究

    • Author(s)
      大島里恵、森 巧一、古川恭子、坂井健男、森 裕二
    • Organizer
      第59回(平成25年度)日本薬学会東海支部大会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] Gymnocin–AのFGH環フラグメントの合成研究

    • Author(s)
      森 巧一、大島里恵、古川恭子、高橋 薫、坂井健男、森 裕二
    • Organizer
      日本プロセス化学会2013サマーシンポジウム
    • Place of Presentation
      つくば
    • Related Report
      2013 Research-status Report
  • [Presentation] Gymnocin-Aの全合成研究

    • Author(s)
      坂井健男、松下真吾、浅野晴日、大島里恵、森 巧一、森 裕二
    • Organizer
      第55回天然有機化合物討論会
    • Place of Presentation
      京都
    • Related Report
      2013 Research-status Report
  • [Presentation] Gymnocin-AのFGH環フラグメントの合成

    • Author(s)
      森 巧一、大島里恵、坂井健男、森 裕二
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] 第3級アルコールのWilliamson型エーテル環化反応とGymnocin–AのKLMNフラグメントの合成

    • Author(s)
      浅野晴日、谷本美樹、安西志織、坂井健男、森 裕二
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] TMSジアゾメタンを用いた位置・立体選択的環拡大反応の反応機構

    • Author(s)
      坂井健男、伊藤聡志、古田大貴、河原祐樹、森 裕二
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] Gymnocin-AのABC環フラグメントの合成

    • Author(s)
      松下真吾、正木 理、坂井健男、森 裕二
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] Gymnocin-AのF/K環ユニットの合成

    • Author(s)
      大島里恵、古川恭子、坂井健男、森 裕二
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] Gymnocin-AのKLMNフラグメントの合成

    • Author(s)
      浅野晴日、坂井健男、森 裕二
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] Total Synthesis of Gambierol, a Polycyclic Ether Marine Toxin

    • Author(s)
      Yuji Mori
    • Organizer
      2nd Annual World Congress of Marine Biotechnology-2012
    • Place of Presentation
      Dalian, China
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 海洋産ポリ環状エーテル天然物の全合成

    • Author(s)
      森 裕二
    • Organizer
      日本薬学会北陸支部特別講演会
    • Place of Presentation
      金沢
    • Related Report
      2012 Research-status Report
    • Invited
  • [Remarks] 名城大学教員情報

    • URL

      https://kyoinjoho.meijo-u.ac.jp/search/profile/ja.d3b102b78467f638.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] 分子設計化学研究室

    • URL

      http://www-yaku.meijo-u.ac.jp/Research/Laboratory/mol_des/MoriLab/Top_Page.html

    • Related Report
      2013 Research-status Report
  • [Remarks] 名城大学 教員情報

    • URL

      https://kyoinjoho.meijo-u.ac.jp/search/profile/ja.d3b102b78467f638.html

    • Related Report
      2013 Research-status Report

URL: 

Published: 2013-05-31   Modified: 2019-07-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi