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Development of efficient synthetic method for the natural product possessing sequential chiral quaternary carbons.

Research Project

Project/Area Number 20790020
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKyoto Pharmaceutical University

Principal Investigator

KAWAI Nobuyuki  Kyoto Pharmaceutical University, 薬学部, 助教 (10411034)

Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2009: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2008: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords合成化学 / 癌 / 薬学 / 有機化学
Research Abstract

Synthesis of platencimycin and bicyclolactone unit of shimalacton possessing sequential quaternary carbons was investigated. In the former, the tri cyclic compound possessing the desired quaternary carbon was obtained with a high selectivity by heating the precursor which consists the diene unit possessing cyclopentane and the dienophile unit possessing tri-substituted alkene at 200℃. In the latter, by utilizing transannular cyclization of the lactone, the cyclopentane derivative was obtained as a sole product with the desired stereochemistry.

Report

(3 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • Research Products

    (22 results)

All 2010 2009 2008 2001

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (16 results)

  • [Journal Article] Lewis acid-catalyzed intramolecular amination via 1, 3-chirality transfer2009

    • Author(s)
      Nobuyuki Kawai, Ryuzou Abe, Jun'ichi Uenishi
    • Journal Title

      Tetrahedron Letters 50

      Pages: 6580-6583

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] An efficient Synthesis of 2 - and 2, 6-Substituted Piperidines Using PdII-Catalyzed 1, 3-Chirality Transfer Reactions.2009

    • Author(s)
      Sudhir M. Hande, Nobuyuki Kawai, Jun'ichi Uenishi
    • Journal Title

      J. Org. Chem. 74

      Pages: 244-253

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Lewis acid-catalyzed intramolecular amination via 1,3-chirality transfer2009

    • Author(s)
      Nobuyuki Kawai, Ryuzou Abe, Jun'ichi Uenishi
    • Journal Title

      Tetrahedron Letters 50

      Pages: 6580-6583

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An efficient synthesis of 2- and 2, 6- substituted piperidines using Pd^<II>-Catalyzed 1, 3-chirality transfer reaction2009

    • Author(s)
      Sudhir M. Hande, Nobuyuki Kawai and Jun'ichi Uenishi
    • Journal Title

      Journal of Organic Chemistry 74

      Pages: 244-253

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereochemistry and Mechanistic Study of Intramolecular Pd II-Catalyzed Oxypalladation and 1, 3-Chirality Transfer Reactions.2008

    • Author(s)
      Jun'ichi Uenishi, Yogesh S. Vikhe, Nobuyuki Kawai
    • Journal Title

      Chem. Asian J. 3

      Pages: 473-484

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereochemistry and Mechanistic Study of Intramolecular Pd^<II>-Catalyzed Oxypalladation and 1, 3-Chirality Transfer Reactions2008

    • Author(s)
      Jun'ichi Uenishi, Yogesh S. Vikhe, Nobuyuki Kawai
    • Journal Title

      Chemistry - An Asian Journal 3

      Pages: 473-484

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] 分子内環化によるシクロペンタン環の立体選択的合成法の研究2010

    • Author(s)
      畑中惇志., 河井伸之., 上西潤一
    • Organizer
      難病克服を目指した分子基盤創薬科学の開拓成果発表会
    • Place of Presentation
      京都(日本)
    • Year and Date
      2010-03-15
    • Related Report
      2009 Annual Research Report
  • [Presentation] 1, 3-Chirality Transfer on Lewis Acids Catalyzed Intramolecular Amino Substitution.2010

    • Author(s)
      Nobuyuki Kawai, Mika Matsuda, Ryuzou Abe, Jun-ichi Uenishi
    • Organizer
      The 21st French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      Kyoto
    • Related Report
      2009 Final Research Report
  • [Presentation] Bi(OTf)3を触媒とする光学活性テトラヒドロイソキノリン誘導体の合成2010

    • Author(s)
      松田望花, 阿部隆三, 河井伸之, 上西潤一
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Related Report
      2009 Final Research Report
  • [Presentation] 2価Pd触媒によるドミノ型環化反応2010

    • Author(s)
      藤倉悠平, 河井伸之, 上西潤一
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Related Report
      2009 Final Research Report
  • [Presentation] 触媒的分子内1, 3-不斉転写反応による窒素環化合物の合成2010

    • Author(s)
      河井伸之, 阿部隆三, 松田望花, 上西 潤一
    • Organizer
      難病克服を目指した分子基盤創薬科学の開拓成 果発表会
    • Place of Presentation
      京都
    • Related Report
      2009 Final Research Report
  • [Presentation] 2位2'位で連結された光学活性THF, THP環化合物の合成2010

    • Author(s)
      藤倉悠平, 河井伸之, 上西潤一
    • Organizer
      難病克服を目指した分子基盤創薬科学の開拓成果発表会
    • Place of Presentation
      京都
    • Related Report
      2009 Final Research Report
  • [Presentation] 光学活性テトラヒドロイソキノリン誘導体の新規合成法の開発2010

    • Author(s)
      松田望花, 阿部隆三, 河井伸之, 上西潤一
    • Organizer
      難病克服を目指した分子基盤創薬科学の開拓成 果発表会
    • Place of Presentation
      京都
    • Related Report
      2009 Final Research Report
  • [Presentation] 1, 3-Chirality Transfer on Lewis Acids Catalyzed Intramolecular Amino Substitution.2009

    • Author(s)
      Nobuyuki Kawai, Ryuzou Abe, Mika Matsuda, Sudhir Mahadeo Hande, Jun-ichi Uenishi
    • Organizer
      11th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-11)
    • Place of Presentation
      Kyoto
    • Related Report
      2009 Final Research Report
  • [Presentation] ルイス酸触媒によるキラルな2級アリルアルコールへの窒素求核剤の分子内SN2'反応2009

    • Author(s)
      河井伸之, 阿部隆三, 松田望花, Sudhir Mahadeo Hande, 上西潤一
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢
    • Related Report
      2009 Final Research Report
  • [Presentation] 1, 3-不斉転写を伴う触媒的環化反応による光学活性な1位置換テトラヒドロイソキノリンの合成研究2009

    • Author(s)
      河井伸之, 阿部隆三, 松田望花, 上西潤一
    • Organizer
      第59回日本薬学会近畿支部大会
    • Place of Presentation
      大阪
    • Related Report
      2009 Final Research Report
  • [Presentation] ビスマストリフラートを触媒としたキラルなアリルコールへの立体選択的分子内直接アミノ置換反応2009

    • Author(s)
      阿部隆三, 松田望花, 河井伸之, 上西潤一
    • Organizer
      第36回有機反応懇談会
    • Place of Presentation
      神戸
    • Related Report
      2009 Final Research Report
  • [Presentation] Stereochemistry and Mechanistic Study of Intramolecular Pd^<II>-Catalyzed Oxypalladation and 1, 3-Chirality Transfer Reactions2008

    • Author(s)
      Yogesh S. Vikhe, Nobuyuki Kawai, Jun'ichi Uenishi
    • Organizer
      International Symposium on Integrated Medicinal Science
    • Place of Presentation
      京都(日本)
    • Year and Date
      2008-12-13
    • Related Report
      2008 Annual Research Report
  • [Presentation] Stereochemistry and mechanistic study of intramolecular PdII-catalyzed oxypalladation and 1, 3-chirality-transfer reaction.2008

    • Author(s)
      Yogesh S. Vikhe, Nobuyuki Kawai, Jun' ichi Uenishi
    • Organizer
      International Symposium on Integrated Medicinal Science
    • Place of Presentation
      Kyoto
    • Related Report
      2009 Final Research Report
  • [Presentation] Total synthesis of (-)-zampanolide.2008

    • Author(s)
      Takuya Iwamoto, Nobuyuki Kawai, Jun' ichi Uenishi
    • Organizer
      International Symposium on Integrated Medicinal Science
    • Place of Presentation
      Kyoto
    • Related Report
      2009 Final Research Report
  • [Presentation] Asymmetric synthesis of (+)- and (-)-coniine2008

    • Author(s)
      Sudhir M. Hande、河井伸之、上西潤 一
    • Organizer
      第58回日本薬学会近畿支部大会
    • Place of Presentation
      神戸
    • Related Report
      2009 Final Research Report
  • [Presentation] 分子内環化によるシクロペンタン環の合成2001

    • Author(s)
      畑中惇志, 河井伸之, 上西潤一
    • Organizer
      難病克服を目指した分子基盤創薬科学の開拓成果発表会
    • Place of Presentation
      京都
    • Related Report
      2009 Final Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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