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Development of a divergent synthesis of 4- and 5-membered heterocycles and its application to the synthesis of bioactive natural product

Research Project

Project/Area Number 24790012
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionKinki University (2013)
Osaka University (2012)

Principal Investigator

MAEGAWA Tomohiro  近畿大学, 薬学部, 准教授 (40363890)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2012: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
KeywordsO,P-アセタール / オキセタン / 複素環合成 / 天然物合成 / 創薬化学 / 複素環化合物 / アゼチジン
Research Abstract

Heterocyclic compounds are utilized in pharmaceuticals, agrochemicals and functional materials. Recently, oxygen-containing 4-membered heterocycles, oxetane, has been reported as a useful skeleton to improve a pharmaceutical quality. We developed a facile oxetane synthesis using O,P-acetal consisted of phosphorous and oxygen as a key intermediate. The feature of this method is eco-conscious double use of phosphorous atom in one reaction. We also succeeded in synthesizing natural product having anticancer activity in short steps using our method.

Report

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

    (7 results)

All 2013 2012 Other

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (6 results)

  • [Journal Article] A Method for Efficient Synthesis of Highly-Substituted Oxetan- and Azetidin-, Dihydrofuran- and Pyrrolidin-3-ones and Its Application to the Synthesis of (±)-Pseudodeflectusin2012

    • Author(s)
      藤岡弘道 他
    • Journal Title

      Organic Letters

      Volume: 14 Issue: 18 Pages: 4798-4801

    • DOI

      10.1021/ol302096j

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Intramolecular Cyclization Using Phosphonate-stabilized Anion : Efficient Synthesis of Highly-Substituted Oxetan- and Azetidin-, Dihydrofuran- and Pyrrolidin-3-ones and Its Application2013

    • Author(s)
      前川智弘、大竹和樹、廣澤渓一、後藤章広、藤岡弘道
    • Organizer
      10^<th> International Symposium on Carbanion Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2013-09-24
    • Related Report
      2013 Final Research Report
  • [Presentation]2012

    • Author(s)
      前川智弘、大竹和樹、廣澤渓一、後藤章広、藤岡弘道
    • Organizer
      第6回武田科学振興財団薬科学シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2012-09-13
    • Related Report
      2013 Final Research Report
  • [Presentation]2012

    • Author(s)
      前川智弘、大竹和樹、廣澤渓一、後藤章広、藤岡弘道
    • Organizer
      日本プロセス化学会2012サマーシンポジウム
    • Place of Presentation
      京都
    • Year and Date
      2012-07-20
    • Related Report
      2013 Final Research Report
  • [Presentation]2012

    • Author(s)
      前川智弘、大竹和樹、廣澤渓一、後藤章広、藤岡弘道
    • Organizer
      第10回次世代担う有機化学シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2012-05-11
    • Related Report
      2013 Final Research Report
  • [Presentation] Intramolecular Cyclization Using Phosphonate-stabilized Anion: Efficient Synthesis of Highly-Substituted Oxetan- and Azetidin-, Dihydrofuran- and Pyrrolidin-3-ones and Its Application

    • Author(s)
      Tomohiro Maegawa, Kazuki Otake, Keiichi Hirosawa, Akihiro Goto, and Hiromichi Fujioka
    • Organizer
      The 10th International Symposium on Carbanion Chemistry (ISCC-10)
    • Place of Presentation
      同志社大学(京都府)
    • Related Report
      2013 Annual Research Report
  • [Presentation] O,P-アセタールを利用したオキセタン-3-オン及びジヒドロフラン-3-オン誘導体の新規合成法の開発とその応用

    • Author(s)
      前川智弘
    • Organizer
      第10回次世代を担う有機化学シンポジウム
    • Place of Presentation
      大阪大学
    • Related Report
      2012 Research-status Report

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

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