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Synthetic Studies on Bioactive Polycyclic Ethers

Research Project

Project/Area Number 21590029
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionMeijo University

Principal Investigator

MORI Yuji  名城大学, 薬学部, 教授 (40121511)

Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2011: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2009: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsポリ環状エーテル / 全合成 / ガンビエロール / シガテラ毒 / 神経毒 / 海洋天然物 / ポリテトラヒドロピラン / 収束合成 / オキシラニルアニオン / Gambierdiscus toxicus / gambierol / 環拡大反応 / 海洋ポリエーテル / 海洋毒 / シガテラ / 6-エンド閉環反応
Research Abstract

Ciguatera poisoning is a toxicological syndrome resulting from the ingestion of seafood contaminated by certain toxic polycyclic ethers produced by the epiphytic dinoflagellate Gambierdiscus toxicus. The toxin suite comprises ciguatoxins, maitotoxin, and gambierol. Gambierol consists of a ladder-shaped trans-fused octacyclic ring system with 18 stereogenic centers. The total synthesis of gambierol has been achieved utilizing an oxiranyl anion strategy in an iterative manner. The synthetic route includes direct carbon. carbon formation on epoxides, sulfonyl. assisted 6.endo cyclization, and ring expansion reaction of tetrahydropyranyl rings to oxepanes to forge the polycyclic skeleton of the target molecule.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (44 results)

All 2012 2011 2010 2009 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results) Presentation (34 results) Remarks (1 results)

  • [Journal Article] A Convergent Strategy for the Synthesis of Polycyclic Ethers by Using Oxiranyl Anions Takeo Sakai2011

    • Author(s)
      Ai Sugimoto, Yuji Mori
    • Journal Title

      Organic Lett

      Volume: 13 Issue: 21 Pages: 5850-5853

    • DOI

      10.1021/ol202467z

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Convergent Strategy for the Synthesis of Polycyclic Ethers by Using Oxiranyl Anions2011

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

      Organic Letters

      Volume: 13 Pages: 5850-5853

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Gambierol2010

    • Author(s)
      Yuji Mori
    • Journal Title

      Heterocycles

      Volume: 81 Issue: 10 Pages: 2203-2228

    • DOI

      10.3987/rev-10-676

    • NAID

      40017284215

    • Related Report
      2011 Final Research Report 2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Gambierol by Using Oxiranyl Anions2010

    • Author(s)
      Hiroki Furuta, Yuki Hasegawa, Mariko Hase, Yuji Mori
    • Journal Title

      Chem.-Eur. J.

      Volume: 16 Issue: 25 Pages: 7586-7595

    • DOI

      10.1002/chem.201000497

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Gambierol by Using Oxiranyl Anions2010

    • Author(s)
      Hiroki Furuta
    • Journal Title

      Chem.Eur.J.

      Volume: 16 Pages: 7586-7595

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Gambierol2009

    • Author(s)
      Hiroki Furuta, Yuki Hasegawa, Yuji Mori
    • Journal Title

      Org. Lett

      Volume: 11 Issue: 19 Pages: 4382-4385

    • DOI

      10.1021/ol9017408

    • NAID

      40017284215

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Conversion of Bromoalkenes into Alkynes by Wet Tetra-n-butylammonium Fluoride2009

    • Author(s)
      Masaru Okutani, Yuji Mori
    • Journal Title

      Masaru Okutani, Yuji Mori J. Org. Chem.

      Volume: 74 Issue: 1 Pages: 442-444

    • DOI

      10.1021/jo802101a

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Conversion of Bromoalkenes into Alkynes by Wet Tetra-n-butylammonium Fluoride2009

    • Author(s)
      Masaru Okutani
    • Journal Title

      Journal of Organic Chemistry 74

      Pages: 442-444

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Gambierol2009

    • Author(s)
      Hiroki Furuta
    • Journal Title

      Organic Letters 11

      Pages: 4382-4385

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] Gymnocin-AのN環の合成研究2012

    • Author(s)
      浅野晴日、坂井健男、森裕二
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-30
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] Gymnocin-AのKLMN環の合成研究2012

    • Author(s)
      古川恭子、坂井健男、森裕二
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-30
    • Related Report
      2011 Final Research Report
  • [Presentation] Gymnocin-AのABC環の合成研究2012

    • Author(s)
      松下真吾、伊藤聡志、坂井健男、森裕二
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-29
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] テトラシアノシクロペンタジエニド類の新規合成法開発2012

    • Author(s)
      坂井健男、瀬尾昭平、森裕二
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] 中員環を含むポリ環状エーテルの新規収束合成法の開発2011

    • Author(s)
      坂井健男、杉本愛、上田光明、森裕二
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島
    • Year and Date
      2011-11-08
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] Total Synthesis of Gambierol2011

    • Author(s)
      Yuji Mori
    • Organizer
      International Symposium on Green Biotechnology
    • Place of Presentation
      Nagoya
    • Year and Date
      2011-10-20
    • Related Report
      2011 Final Research Report
  • [Presentation] ポリ環状エーテルの収束的合成法の開発とギムノシン-A合成への応用2011

    • Author(s)
      坂井健男、杉本愛、古川恭子、森裕二
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪
    • Year and Date
      2011-09-28
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] A Convergent Strategy for the Synthesis of trans-Fused Polycyclic Ethers by Using Oxiranyl Anions2011

    • Author(s)
      Takeo Sakai, Ai Sugimoto, Yuji Mori
    • Organizer
      The 2nd International Symposium on Process Chemistry
    • Place of Presentation
      Kyoto
    • Year and Date
      2011-08-12
    • Related Report
      2011 Final Research Report
  • [Presentation] ジアゾメタン類を用いた環拡大反応による78員環エーテル合成2011

    • Author(s)
      伊藤聡志、立松大輝、坂井健男、森裕二
    • Organizer
      第57回(平成23年度)日本薬学会東海支部大会
    • Place of Presentation
      名古屋
    • Year and Date
      2011-07-09
    • Related Report
      2011 Final Research Report
  • [Presentation] Gymnocin-AのFGH環、KLM環に共通するメチル基を有する三環性モデルの構築2011

    • Author(s)
      上田光明、坂井健男、森裕二
    • Organizer
      第57回(平成23年度)日本薬学会東海支部大会
    • Place of Presentation
      名古屋
    • Year and Date
      2011-07-09
    • Related Report
      2011 Final Research Report
  • [Presentation] Gymnocin-AのFGH環、KLM環のフラグメント合成2011

    • Author(s)
      古川恭子、坂井健男、森裕二
    • Organizer
      第57回(平成23年度)日本薬学会東海支部大会
    • Place of Presentation
      名古屋
    • Year and Date
      2011-07-09
    • Related Report
      2011 Final Research Report
  • [Presentation] TMSCHN_2を用いた環拡大反応による8員環エーテル合成2011

    • Author(s)
      伊藤聡志、立松大輝、坂井健男、森裕二
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] Gymnocin-AのABC環の合成研究2011

    • Author(s)
      松下真吾、伊藤聡志、坂井健男、森裕二
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] Gymnocin-AのFGH環、KLM環に共通する環システムの合成研究2011

    • Author(s)
      古川恭子、上田光明、坂井健男、森裕二
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] オキシラニルアニオンの求核置換反応を鍵とする環状ポリエーテルの収束的合成法を応用した8環性ポリエーテル合成2011

    • Author(s)
      坂井健男、杉本愛、森裕二
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-28
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] 環状ポリエーテルの収束的合成法開発と8環性ポリエーテル合成への応用2010

    • Author(s)
      坂井健男、杉本愛、森裕二
    • Organizer
      第41回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋
    • Year and Date
      2010-11-06
    • Related Report
      2011 Final Research Report
  • [Presentation] 環状ポリエーテルの収束的合成法の開発と8環性ポリエーテル合成への応用2010

    • Author(s)
      坂井健男、杉本愛、森裕二
    • Organizer
      第41回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋
    • Year and Date
      2010-11-06
    • Related Report
      2010 Annual Research Report
  • [Presentation] 収束型合成法を利用した8環性ポリエーテル合成2010

    • Author(s)
      杉本愛、坂井健男、森裕二
    • Organizer
      第56回(平成22年度)日本薬学会東海支部大会
    • Place of Presentation
      岐阜
    • Year and Date
      2010-07-03
    • Related Report
      2011 Final Research Report
  • [Presentation] 収束型合成法を利用した8環性ポリエーテル合成2010

    • Author(s)
      杉本愛、坂井健男、森裕二
    • Organizer
      第56回日本薬学会東海支部大会
    • Place of Presentation
      岐阜
    • Year and Date
      2010-07-03
    • Related Report
      2010 Annual Research Report
  • [Presentation] オキシラニルアニオンを用いたポリ環状エーテルの収束型合成法の開発研究2010

    • Author(s)
      杉本愛、森裕二
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] ガンビエロールの全合成2009

    • Author(s)
      長谷川裕基、森裕二、古田大貴
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢
    • Year and Date
      2009-11-17
    • Related Report
      2011 Final Research Report 2009 Annual Research Report
  • [Presentation] オキシラニルアニオンを用いたポリ環状エーテルの収束型合成法の開発2009

    • Author(s)
      杉本愛、森裕二
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢
    • Year and Date
      2009-11-17
    • Related Report
      2011 Final Research Report 2009 Annual Research Report
  • [Presentation] Total Synthesis of Gambierol2009

    • Author(s)
      Yuki Hasegawa, Hiroki Furuta, Yuji Mori
    • Organizer
      The 11^<th> International Kyoto Conference on New Aspect of Organic Chemistry(IKCOC-11)
    • Place of Presentation
      京都
    • Year and Date
      2009-11-11
    • Related Report
      2011 Final Research Report
  • [Presentation] Convergent Strategy for trans-Fused Polycyclic Ethers Using Oxiranyl Anion Coupling2009

    • Author(s)
      Ai Sugimoto, Yuji Mori
    • Organizer
      The 11^<th> International Kyoto Conference on New Aspect of Organic Chemistry(IKCOC-11)
    • Place of Presentation
      京都
    • Year and Date
      2009-11-11
    • Related Report
      2011 Final Research Report
  • [Presentation] Convergent Strategy for trans-Fused Polycyclic Ethers Using Oxiranyl Anion Coupling2009

    • Author(s)
      森裕二
    • Organizer
      The 11^<th> International Kyoto Conference on New Aspect of Organic Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2009-11-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] Total Synthesis of Gambierol2009

    • Author(s)
      森裕二
    • Organizer
      The 11^<th> International Kyoto Conference on New Aspect of Organic Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2009-11-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] ガンビエロールの全合成2009

    • Author(s)
      古田大貴、長谷川裕基、森裕二
    • Organizer
      第40回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      岐阜
    • Year and Date
      2009-11-08
    • Related Report
      2011 Final Research Report 2009 Annual Research Report
  • [Presentation] オキシラニルアニオンを用いたポリ環状エーテルの収束型合成法の開発2009

    • Author(s)
      杉本愛、森裕二
    • Organizer
      第40回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      岐阜
    • Year and Date
      2009-11-08
    • Related Report
      2011 Final Research Report 2009 Annual Research Report
  • [Presentation] ガンビエロールの全合成2009

    • Author(s)
      古田大貴、長谷川裕基、森裕二
    • Organizer
      第51回天然有機化合物討論会
    • Place of Presentation
      名古屋
    • Year and Date
      2009-10-09
    • Related Report
      2011 Final Research Report 2009 Annual Research Report
  • [Presentation] Total synthesis of gambierol2009

    • Author(s)
      Yuki Hasegawa, Hiroki Furuta, Yuji Mori
    • Organizer
      The 6^<th> Nagoya-Nanjing-Shenyang Symposium of Pharmaceutical Sciences
    • Place of Presentation
      名古屋
    • Year and Date
      2009-09-14
    • Related Report
      2011 Final Research Report
  • [Presentation] Convergent strategy for trans-fused polycyclic ethers using oxiranyl anion coupling2009

    • Author(s)
      Ai Sugimoto, Yuji Mori
    • Organizer
      The 6^<th> Nagoya-Nanjing-Shenyang Symposium of Pharmaceutical Sciences
    • Place of Presentation
      名古屋
    • Year and Date
      2009-09-14
    • Related Report
      2011 Final Research Report
  • [Presentation] ガンビエロールの全合成2009

    • Author(s)
      古田大貴、長谷川裕基、森裕二
    • Organizer
      第55回(平成21年度)日本薬学会東海支部大会
    • Place of Presentation
      名古屋
    • Year and Date
      2009-07-11
    • Related Report
      2011 Final Research Report
  • [Presentation] ポリ環状エーテルの収束型合成法の開発2009

    • Author(s)
      杉本愛、森裕二
    • Organizer
      第55回(平成21年度)日本薬学会東海支部大会
    • Place of Presentation
      名古屋
    • Year and Date
      2009-07-11
    • Related Report
      2011 Final Research Report 2009 Annual Research Report
  • [Presentation] ガンビエロールの全合成研究2009

    • Author(s)
      森裕二
    • Organizer
      第55回(平成21年度)日本薬学会東海支部大会
    • Place of Presentation
      名古屋
    • Year and Date
      2009-07-11
    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • Related Report
      2011 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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