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Catalytic Asymmetric Synthesis of Biologically Important Molecules

Research Project

Project/Area Number 02453137
Research Category

Grant-in-Aid for General Scientific Research (B)

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

Principal Investigator

SHIBASAKI Masakatsu  Hokkaido Univ.Fac.Pharamac.Sci・Professor, 薬学部, 教授 (30112767)

Co-Investigator(Kenkyū-buntansha) SATO Yoshihiro  Hokkaido Univ.Fac.Pharmac.Sci・Instructor, 薬学部, 教務職員 (90226019)
SASAI Hiroaki  Hokkaido Univ.Fac.Pharmac.Sci・Instructor, 薬学部, 助手 (90205831)
袖岡 幹子  北海道大学, 薬学部, 助手 (60192142)
Project Period (FY) 1990 – 1991
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥5,800,000 (Direct Cost: ¥5,800,000)
Fiscal Year 1991: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 1990: ¥4,400,000 (Direct Cost: ¥4,400,000)
KeywordsHeck Reaction / Catalytic Asymmetric Synthesis / Decalin Derivatives / Hydrindan Derivatives / Capnellenol / Marine Natural Product / カプネレノ-ル / 不斉ヘック反応 / 不斉πーアリルパラジウム / カプネランアルコ-ル / アザディラクチン
Research Abstract

Previously we developed an asymmetric Heck reaction, in which the cis-decalin derivative was obtained in 45% ee. Now we have succeeded in improving the above-mentioned asymmetric Heck reaction as shown below.
Furthermore, we have accomplished a catalytic asymmetric synthesis of capnellenols 5 and 6 by utilizing an asymmetric Heck reaction. On the other hand, the cis-decalin derivative 7 has been found to be synthesized in 83% ee through the pi-allylpalladium intermediate.

Report

(3 results)
  • 1991 Annual Research Report   Final Research Report Summary
  • 1990 Annual Research Report
  • Research Products

    (7 results)

All Other

All Publications (7 results)

  • [Publications] Yoshihiro Sato: "On the Role of Silver Salts in Asymmetric Heck-type Reaction.A Greatly Improued Catalytic Asymmetric Synthesis of Cis-Decclir Derivatiues" Chemistry Letters. 1953-1954 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Katsuji Kagechika: "Asymmetric Heck Reaction.A Catalytic Asymmetric Synthesis of the Key Intirmediate for DELTA^<9(12)>-Capnellener 3beta,8beta,10alpha-triol and DELTA9^<9(12)>-Capnel〓ne-3beta,8beta,10alpha,14-litrol." The Journal of Organic Chemistry. 56. 4093-4094 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Yoshihiro Soto: "On the Role of Silver Salts in Asymmetric Heck-type Reaction. A Greatly Improved Catalytic Asymmetric Synthesis of cis-Decalin Derivatives" Chemistry Letters. 56. 1953-1954 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Katsuji Kagechika: "Asymmetric Heck Reaction. A Catalytic Asymmectric Synthesis of the Key Intermediate for DELTA^<9(12)>-Caonellene-3beta, 8beta, 10alpha-triol and DELTA^<9(12)>-Caonellene-3bata, 8beta, 10alpha, 14-tetrol" 4093-4094 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Yoshihiro Sato: "On the Role of Silver Salts in Asymmetric Heckーtype Reaction.A Greathy Improved Catahytic Asymmetric Synthesis of Cis Decalin Deriratiues" Chemistry Letters. 1953-1954 (1990)

    • Related Report
      1991 Annual Research Report
  • [Publications] Katsuji Kagechika: "Asymmetric Heck Reaction.A Catalytic Asymmetric Syntheois of the key Intermedacte for △^<9(12)>ーCaponellener 3β,8β,10αーtriol and △^<9(12)>ーCapnelleneー3β,8β,10α,14ーeitrol" The Journal of oiganic Chimistry. 56. 4093-4094 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Yoshihiro Sato: "On the Role of Siluer Salts in Asymmetric Heckーtype Reaction.A Greatly Improued catalytic.Asymmetric Synthesis of c<is>___ーーDecalin Decuvetiucs" Chemistry Letters. 1953-1954 (1990)

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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