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Development of regioselective reactions of substituted benzynes and its application to synthesis of polysubstituted fused aromatic compounds

Research Project

Project/Area Number 19590008
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionUniversity of Shizuoka

Principal Investigator

AKAI Shuji  University of Shizuoka, 薬学部, 教授 (60192457)

Project Period (FY) 2007 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2008: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2007: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywordsベンザイン / 縮合芳香環 / ケイ素 / Diels-Alder反応 / フラン / 位置選択性 / 求核付加反応 / 檜山カップリング / ケイ素基 / 1,8-ジヒドロキシナフタレン
Research Abstract

天然物や合成医薬品には複数のベンゼン環が並び, その環上に多種類の置換基を持つ縮合芳香環化合物が多数存在するが, これらの合成は必ずしも容易ではない. 本研究では, ベンザインの反応位置の制御法を開発することで, この問題点の解決に取り組んだ. その結果, シリル基を利用して, ベンザインへの環状付加反応や求核付加反応の位置を制御できることを見出した. さらに, 同シリル基を他の置換基に変換する方法を開発した. これら二つの反応によって, 多置換縮合芳香環構造の効率的な新合成が可能になった.

Report

(3 results)
  • 2008 Annual Research Report   Final Research Report ( PDF )
  • 2007 Annual Research Report
  • Research Products

    (22 results)

All 2009 2008 2007

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (17 results)

  • [Journal Article] Synthesis of Biaryl Compounds through Three-Component Assembly : Ambidentate Effect of the tert-Butyldimethylsilyl Group for Regioselective Diels-Alder and Hiyama Coupling Reactions2008

    • Author(s)
      Akai, Shuji ; Ikawa, Takashi ; Takayanagi, Sho-ichi ; Morikawa, Yuki ; Mohri, Shinya ; Tsubakiyama, Masaya ; Egi, Masahiro ; Wada, Yasufumi ; Kita, Yasuyuki
    • Journal Title

      Angew. Chem. Int. Ed. 47

      Pages: 7673-7676

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Biaryl Compounds through Three-Component Assembly : Ambidentate Effect of the tert-Butyldimethylsilyl Group for Regioselective Diels-Alder and Hiyama Coupling Reactions2008

    • Author(s)
      Shuji, Akai, et al.
    • Journal Title

      Angew. Chem. Int. Ed. 47

      Pages: 7673-7676

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (±)-γ-Rubromycin on the Basis of Two Aromatic Pummerer-Type Reactions2007

    • Author(s)
      Akai, Shuji ; Kakiguchi, Keisuke ; Nakamura, Yuka ; Kuriwaki, Ikumi ; Dohi, Toshifumi ; Harada, Shusaku ; Kubo, Ozora ; Morita, Nobuyoshi ; Kita, Yasuyuki
    • Journal Title

      Angew. Chem. Int. Ed. 46

      Pages: 7458-7461

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Recent Advances in Pummerer Reactions2007

    • Author(s)
      Akai, Shuji ; Kita, Yasuyuki
    • Journal Title

      Topics Curr. Chem

      Pages: 35-76

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of(±)-γ-Rubromycin on the Basis of Two Aromatic Pummerer-Type Reactions2007

    • Author(s)
      Shuji Akai, et. al.
    • Journal Title

      Angew. Chem. Int. Ed. 46

      Pages: 7458-7461

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] シリル置換ベンザインの位置選択的Diels-Alder反応 : Aloinの合成研究2009

    • Author(s)
      守川由起, 井川貴詞, 高柳祥一, 毛利真也, 赤井周司
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-28
    • Related Report
      2008 Final Research Report
  • [Presentation] シリル置換ベンザインの位置選択的Diels-Alder反応 : Aloinの合成研究2009

    • Author(s)
      守川由起, 赤井周司, 他
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都市
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] ベンザインへのアミン類の求核付加反応における位置制御法の開発2009

    • Author(s)
      井川貴詞, 毛利真也, 森田真介, 赤井周司
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-27
    • Related Report
      2008 Final Research Report
  • [Presentation] ベンザインヘのアミン類の求核付加反応における位置制御法の開発2009

    • Author(s)
      井川貴詞, 赤井周司, 他
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都市
    • Year and Date
      2009-03-27
    • Related Report
      2008 Annual Research Report
  • [Presentation] 置換ベンザインへの求核付加反応の位置制御2008

    • Author(s)
      井川貴詞, 毛利真也, 森田真介, 赤井周司
    • Organizer
      平成20年度日本薬学会東海支部例会
    • Place of Presentation
      静岡
    • Year and Date
      2008-12-06
    • Related Report
      2008 Final Research Report
  • [Presentation] 置換ベンザインヘの求核付加反応の位置制御2008

    • Author(s)
      毛利真也, 赤井周司, 他
    • Organizer
      平成20年度日本薬学会東海支部例会
    • Place of Presentation
      静岡県立大学
    • Year and Date
      2008-12-06
    • Related Report
      2008 Annual Research Report
  • [Presentation] 多置換縮合芳香族化合物の位置制御構築2008

    • Author(s)
      赤井周司
    • Organizer
      第39回中化連合秋季大会依頼講演
    • Place of Presentation
      名古屋大学(講演時間40分)
    • Year and Date
      2008-11-09
    • Related Report
      2008 Final Research Report
  • [Presentation] 多置換縮合芳香族化合物の位置制御構築2008

    • Author(s)
      赤井 周司
    • Organizer
      第39回中化連合秋季大会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2008-11-09
    • Related Report
      2008 Annual Research Report
  • [Presentation] Regiocontrolled Construction of Highly Functionalized Polyaromatic Compounds : Aromatic Pummerer-type Reactions and Regioselective Diels-Alder Reactions of Benzynes2008

    • Author(s)
      Akai, Shuji
    • Place of Presentation
      Lecture at Duke Univ., Duhram, North Calorina, USA(50 min)
    • Year and Date
      2008-07-14
    • Related Report
      2008 Final Research Report
  • [Presentation] Regiocontrolled Construction of Highly Functionalized Polyaromatic Compounds : Aromatic Pummerer-type Reactions and Benzyne Reactions2008

    • Author(s)
      Akai, Shuji
    • Place of Presentation
      Lecture at MIT Cambridge, Massatusettu, USA(40 min)
    • Year and Date
      2008-07-11
    • Related Report
      2008 Final Research Report
  • [Presentation] アリルジメチルシリル置換ベンザインの位置選択的Diels-Alder反応を用いる多置換ナフタレン類の合成2008

    • Author(s)
      赤井周司, 高柳祥一, 井川貴詞, 守川由起, 毛利真也, 江木正浩, 和田康史, 北泰行
    • Organizer
      日本薬学会第128年会
    • Place of Presentation
      横浜
    • Year and Date
      2008-03-27
    • Related Report
      2008 Final Research Report 2007 Annual Research Report
  • [Presentation] 多置換縮合芳香族化合物の位置制御構築 : こだわりの全合成2008

    • Author(s)
      赤井周司
    • Organizer
      新潟薬科大学特別講義
    • Place of Presentation
      (講演時間90分)
    • Year and Date
      2008-02-15
    • Related Report
      2008 Final Research Report
  • [Presentation] Regioselective Diels-Alder Reactions of Silylbenzynes : Convergent Synthesis of Polysubstituted Biaryls2008

    • Author(s)
      Takayanagi, Sho-ichi ; Ikawa, Takashi ; Morikawa, Yuki ; Mohri, Shinya ; Tsubakiyama, Masaya ; Egi, Masahiro ; Akai, Shuji ; Wada, Yasufumi ; Kita, Yasuyuki
    • Organizer
      The first International Symposium on Process Chemistry (ISPC08)
    • Place of Presentation
      Kyoto
    • Related Report
      2008 Final Research Report
  • [Presentation] Regioselective Diels-Alder Reactions of Silylbenzynes : Convergent Synthesis of Polysubstituted Biaryls2008

    • Author(s)
      高柳祥一, 赤井周司, 他
    • Organizer
      The first International Symposium on Process Chemistry
    • Place of Presentation
      京都市
    • Related Report
      2008 Annual Research Report
  • [Presentation] TBDMSベンザインの位置選択的Diels-Alder反応と檜山カップリングによる置換基導入2007

    • Author(s)
      井川貴詞, 高柳祥一, 毛利真也, 守川由起, 椿山正哉, 江木正浩, 赤井周司
    • Organizer
      平成19年度日本薬学会東海支部例会
    • Place of Presentation
      岐阜
    • Year and Date
      2007-12-08
    • Related Report
      2008 Final Research Report 2007 Annual Research Report
  • [Presentation] シリル置換ベンザインの位置選択的Diels-Alder反応と置換ナフタレン類合成への応用2007

    • Author(s)
      赤井周司, 高柳祥一, 井川貴詞, 守川由起,毛利真也, 椿山正哉, 江木正浩, 和田康史, 北泰行
    • Organizer
      第92回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2007-11-08
    • Related Report
      2008 Final Research Report 2007 Annual Research Report
  • [Presentation] 多置換縮合芳香族化合物の位置制御構築 : 全合成の醍醐味2007

    • Author(s)
      赤井周司
    • Organizer
      岐阜薬科大学薬学会東海支部特別講演会
    • Place of Presentation
      (講演時間90分)
    • Year and Date
      2007-06-27
    • Related Report
      2008 Final Research Report

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Published: 2007-04-01   Modified: 2016-04-21  

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