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Asymmetric Total Synthesis of Bioactive Natural Products via Planar Chiral Enolate

Research Project

Project/Area Number 21790014
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

YOSHIMURA Tomoyuki  Kyoto University, 化学研究所, 助教 (20432320)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2010: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2009: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords有機化学 / 全合成 / 面性不斉 / 面性不斉エノラート / 有機合成化 / 不斉合成 / 生理活性天然 / 有機合成化学 / 生理活性天然物
Research Abstract

Asymmetric intramolecular conjugate addition reaction and intramolecular alkylation reaction via planar chiral enolates were investigated in detail. As a result of various exanimation of reaction conditions, it was found that electron-withdrawing groups in the part of Michael acceptor played an important role in yield and optical purity of products in asymmetric conjugate addition reaction. On the other hand, the substituents on aromatic ring which are adjacent to enolate and electrophilic residue were found to affect yield and optical purity of products in asymmetric intramolecular alkylation reaction. These reactions would be used in the total syntheses of bioactive natural products as a key step.

Report

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

    (23 results)

All 2011 2010 2009 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (18 results) Remarks (1 results)

  • [Journal Article] Asymmetric Carbonyl Migration of a-Amino Acid Derivatives via Memory of Chirality.2011

    • Author(s)
      Teraoka, F., Fuji, K., Ozurk, O., Yoshimura, T., Kawabata,T.
    • Journal Title

      Svnlett

      Pages: 543-546

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Carbonyl Migration of α-Amino Acid Derivatives via Memory of Chirality2011

    • Author(s)
      Fumiteru Teraoka, Kaoru Fuji, Orhan Ozturk, Tomoyuki Yoshimura, Takeo Kawabata
    • Journal Title

      Synlett

      Pages: 543-546

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Insights into Origins of Configurational Stability of Axially Chiral Biaryl Amines with an Intramolecular N-H-N Hydrogen Bond.2010

    • Author(s)
      Hayashi, K., Matubayasi, N., Jiang, C., Yoshimura, T., Majumdar, S., Sasamori, T., Tokitoh, N., Kawabata, T.
    • Journal Title

      J.Org.Chem 75

      Pages: 5031-5036

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Insights into Origins of Configurational Stability of Axially Chiral Biaryl Amines with an Intramolecular N-H-H Hydrogen Bond2010

    • Author(s)
      Kazuhiro Hayashi, Nobuyuki Matsubayashi, Changsheng Jiang, Tomoyuki Yoshimura, Swapan Majumdar, Takahiro Sasamori, Norihiro Tokitoh, Takeo Kawabata
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 75 Pages: 5031-5036

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] 不斉記憶型反応を経由する分子間不斉マイケル付加反応の開発2011

    • Author(s)
      吉岡広泰、吉村智之、川端猛夫
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-30
    • Related Report
      2010 Final Research Report
  • [Presentation] Asymmetric intramolecular conjugate addition via short-lived C-O axially chiral enolate2010

    • Author(s)
      K.Tomohara, T.Yoshimura, T.Kawabata
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2010-12-18
    • Related Report
      2010 Final Research Report
  • [Presentation] Asymmetric intramolecular conjugate addition via short-lived C-O azially chiral enolate2010

    • Author(s)
      友原啓介、吉村智之、川端猛夫
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2010-12-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] Asymmetric synthesis of multisubstituted β-lactamsfrom α-amino acids via memory of chirality using a Cs_2CO_3/EtOH system2010

    • Author(s)
      T.Yoshimura, M.Takuwa, M.Uyama, K.Hayashi, D.Monguchi, T.Sasamori, N.Tokitoh, T.Kawabata
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2010-12-15
    • Related Report
      2010 Final Research Report
  • [Presentation] Asymmetric Synthesis of multisubstituted β-lactams from a-amino acids via memory of chirality using Cs_2CO_3/EtOH system2010

    • Author(s)
      吉村智之、多久和正訓、宇山允人、林一広、門口大輝、笹森貴裕、時任宣博、川端猛夫
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2010-12-15
    • Related Report
      2010 Annual Research Report
  • [Presentation] 不斉記憶型共役付加反応を経由する多置換β-ラクタムの不斉合成2010

    • Author(s)
      楊畔、多久和正訓、宇山允人、友原啓介、林一広、吉村智之、川端猛夫
    • Organizer
      第29回メディシナルケミストリーシンポジウム
    • Place of Presentation
      京都
    • Year and Date
      2010-11-17
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] 短寿命キラルエノラートを経由する四置換炭素含有環状工ーテル類の不斉合成2010

    • Author(s)
      吉村智之、友原啓介、川端猛夫
    • Organizer
      第60回日本薬学会近畿支部総会・大会
    • Place of Presentation
      大阪、摂南大学
    • Year and Date
      2010-10-30
    • Related Report
      2010 Final Research Report
  • [Presentation] 短寿命キラルエノラートを経由する四置換炭素含有環状エーテル類の不斉合成2010

    • Author(s)
      吉村智之、友原啓介、川端猛夫
    • Organizer
      第60回日本薬学会近畿支部総会・大会
    • Place of Presentation
      大阪・摂南大学
    • Year and Date
      2010-10-30
    • Related Report
      2010 Annual Research Report
  • [Presentation] 無機塩基を室温で用いる精密エノラート化学:含窒素複素環の不斉記憶合成2010

    • Author(s)
      吉村智之、多久和正訓、森山克彦、坂井啓紀、楊畔
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2010-10-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] 異常な軸性不斉安定性を持つ水素結合性ビナフチル型分子のラセミ化挙動2010

    • Author(s)
      林一広、松林伸幸、Changsheng Jiang、吉村智之、椿一典、川端猛夫
    • Organizer
      第40回複素化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2010-10-14
    • Related Report
      2010 Annual Research Report
  • [Presentation] Asymmetric Synthesis of Cyclic Ethers via Short-lived C-O Axially Chiral Enolates2010

    • Author(s)
      T.Yoshimura, K.Tomohara, T.Kawabata
    • Organizer
      Japan-Taiwan Joint Symposium on Innovative Synthesis for New Materials Chemistry
    • Place of Presentation
      Uji, Kyoto
    • Year and Date
      2010-10-05
    • Related Report
      2010 Final Research Report
  • [Presentation] Asymmetric Synthesis of Cyclic Ethers via Short-lived C-O Axially Chiral Enolates2010

    • Author(s)
      吉村智之、友原啓介、川端猛夫
    • Organizer
      Japan-Taiwan Joint Symposium on Innovative Synthesis for New Materials Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2010-10-05
    • Related Report
      2010 Annual Research Report
  • [Presentation] C-O軸性不斉エノラートを経由するキラルジヒドロベンゾフラン及びクロマン類の不斉合成2010

    • Author(s)
      吉村智之、友原啓介、川端猛夫
    • Organizer
      第52回天然有機化合物討論会
    • Place of Presentation
      静岡
    • Year and Date
      2010-09-30
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] 不斉記憶型反応を経由した多置換β-ラクタムの不斉合成2010

    • Author(s)
      吉村智之、多久和正訓、宇山允人、友原啓介、林一広、笹森貴裕、時任宣博、川端猛夫
    • Organizer
      第37回有機反応懇談会
    • Place of Presentation
      京都
    • Year and Date
      2010-08-02
    • Related Report
      2010 Annual Research Report
  • [Presentation] 短寿命C-O軸性不斉エノラートを化成中間体とする新規不斉合成法の開発2009

    • Author(s)
      吉村智之、友原啓介、川端猛夫
    • Organizer
      第59回日本薬学会近畿支部総会・大会
    • Place of Presentation
      大阪
    • Year and Date
      2009-10-24
    • Related Report
      2010 Final Research Report
  • [Presentation] 短寿命C-O軸性不斉エノラートを活性中間体とする新規不斉合成法の開発2009

    • Author(s)
      吉村智之、友原啓介、川端猛夫
    • Organizer
      第59回日本薬学会近畿支部総会・大会
    • Place of Presentation
      大阪
    • Year and Date
      2009-10-24
    • Related Report
      2009 Annual Research Report
  • [Presentation] C-O軸性不斉エノラートを経由する四置換炭素含有キラル環状エーテル類の合成2009

    • Author(s)
      吉村智之、友原啓介、川端猛夫
    • Organizer
      第7回次世代を担う有機化学シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2009-07-24
    • Related Report
      2010 Final Research Report
  • [Presentation] Asymmetric Induction via C-O Axially Chiral Enolates2009

    • Author(s)
      K.Tomohara, T.Yoshimura, T.Kawabata
    • Organizer
      11^<th> International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Kyoto
    • Year and Date
      2009-01-11
    • Related Report
      2010 Final Research Report
  • [Remarks] ホームページ等

    • URL

      http://fos.kuicr.kyoto-u.ac.jp/

    • Related Report
      2010 Final Research Report

URL: 

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

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