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Studies on Biomimetic Synthesis of Chloropupukeananin under High-Pressure Conditions and Investigation into High-Pressure Effect in the Diels-Alder reaction

Research Project

Project/Area Number 24790025
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionWaseda University (2013)
Tokyo University of Science (2012)

Principal Investigator

SUZUKI Takahiro  早稲田大学, 理工学術院, 助教 (80367052)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywords有機化学 / 合成化学 / 天然物合成 / Diels-Alder反応 / 超高圧化学 / carbonyl-ene反応 / 生合成模倣 / 全合成
Research Abstract

We have developed the effective synthesis of a bioactive natural product, chloropupukeananin. Since chloropupukeananin possesses a highly-functionalized complex structure, we planned the biomimetic synthesis of chloropupukeananin. Using, chiral vinylallene and MOB as model compounds of biosynthetic precursors, we have achieved the synthesis of model compound of chloropupukeananin by a Diels-Alder/carbonyl-ene reaction cascade under high-pressure conditions and migration of an acyl group. We have also synthesized the key intermediate and fragments of biosynthetic precursors. We have studied the high-pressure Diels-Alder reaction of the biosynthetic intermediate of Lovastatin for the investigation into high-pressure effect in biosynthesis.

Report

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

    (13 results)

All 2014 2013 2012 Other

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (9 results) (of which Invited: 2 results) Remarks (3 results)

  • [Journal Article] Unexpected Diels-Alder/Carbonyl-ene Cascade toward the Biomimetic Synthesis of Chloropupukeananin2013

    • Author(s)
      Takahiro Suzuki, Yuria Miyajima, Kaname Suzuki, Kanako Iwakiri, Masaki Koshimizu, Go Hirai, Mikiko Sodeoka, Susumu Kobayashi
    • Journal Title

      Organic Letters

      Volume: 15 Pages: 1748-1751

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Diels-Alder反応を鍵とする高度に縮環した天然有機化合物の合成研究2014

    • Author(s)
      鈴木孝洋
    • Organizer
      第二回慶應有機化学若手シンポジウム
    • Place of Presentation
      慶応義塾大学矢上キャンパス(横浜)
    • Year and Date
      2014-05-11
    • Related Report
      2013 Final Research Report
  • [Presentation] Diels-Alder反応を鍵とする高度に縮環した天然有機化合物の合成研究2014

    • Author(s)
      鈴木孝洋
    • Organizer
      第二回慶應有機化学若手シンポジウム
    • Place of Presentation
      慶応義塾大学日吉キャンパス(横浜市)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Unexpected Diels-Alder/ Carbonyl-ene Cascade toward the Biomimetic Synthesis of Chloropupukeananin2013

    • Author(s)
      T. Suzuki, Y. Miyajima, K. Suzuki. S. Kobayashi
    • Organizer
      The 15th Asian Chemical Congress (15ACC)
    • Place of Presentation
      Singapore
    • Year and Date
      2013-08-22
    • Related Report
      2013 Final Research Report
  • [Presentation] Unexpected Diels-Alder/Carbonyl-ene Cascade toward the Biomimetic Synthesis of Chloropupukeananin2013

    • Author(s)
      T. Suzuki; Y. Miyajima; K. Suzuki; S. Kobayashi
    • Organizer
      The 15th Asian Chemical Congress (15ACC)
    • Place of Presentation
      Singapore
    • Related Report
      2013 Annual Research Report
  • [Presentation] 多置換ビシクロ[2.2.2]オクタンを含む天然有機化合物の合成研究2012

    • Author(s)
      鈴木孝洋
    • Organizer
      第47回天然物化学談話会
    • Place of Presentation
      熊本
    • Year and Date
      2012-07-05
    • Related Report
      2013 Final Research Report 2012 Research-status Report
  • [Presentation] 逆電子要請型Diels-Alder反応を利用した複雑な天然有機化合物への挑戦2012

    • Author(s)
      鈴木孝洋
    • Organizer
      有機合成化学協会関東支部有機合成化学ミニシンポジウム②
    • Place of Presentation
      早稲田大学西早稲田キャンパス(東京)
    • Year and Date
      2012-06-30
    • Related Report
      2013 Final Research Report
  • [Presentation] Chloropupukeananinの合成研究2012

    • Author(s)
      鈴木孝洋、宮嶋ゆりあ、鈴木要、石見遼、小清水正樹、小林進
    • Organizer
      第63回有機合成化学協会関東支部シンポジウム(理科大シンポジウム)
    • Place of Presentation
      東京理科大学野田キャンパス(千葉)
    • Year and Date
      2012-05-17
    • Related Report
      2013 Final Research Report
  • [Presentation] 逆電子要請型Diels-Alder反応を利用した複雑な天然有機化合物への挑戦2012

    • Author(s)
      鈴木孝洋
    • Organizer
      有機合成化学協会関東支部有機合成化学ミニシンポジウム②
    • Place of Presentation
      早稲田大学、東京
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] Chloropupukeananinの合成研究2012

    • Author(s)
      鈴木孝洋、宮嶋ゆりあ、鈴木 要、石見 遼、小清水正樹、小林 進
    • Organizer
      第63回有機合成化学協会関東支部シンポジウム(理科大シンポジウム)
    • Place of Presentation
      東京理科大学野田キャンパス、千葉
    • Related Report
      2012 Research-status Report
  • [Remarks] 東京理科大学薬学部小林研究室ホームページ

    • URL

      http://www.rs.noda.tus.ac.jp/kobalab/index.html

    • Related Report
      2013 Final Research Report
  • [Remarks] 東京理科大学薬学部小林研究室ホームページ

    • URL

      http://www.rs.noda.tus.ac.jp/kobalab/index.html

    • Related Report
      2013 Annual Research Report
  • [Remarks] 東京理科大学薬学部小林研究室ホームページ

    • URL

      http://www.rs.noda.tus.ac.jp/kobalab/index.html

    • Related Report
      2012 Research-status Report

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

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