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Synthesis of Biologically Active Compounds from Chiral Natural Products

Research Project

Project/Area Number 62870087
Research Category

Grant-in-Aid for Developmental Scientific Research

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

Principal Investigator

SAKAI Kiyoshi  Kyushu University, 薬学部, 教授 (90153840)

Co-Investigator(Kenkyū-buntansha) FUNAKOSHI Kazuhisa  Kyushu University, 薬学部, 助手 (50037579)
SUEMUNE Hiroshi  Kyushu University, 薬学部, 助手 (20095897)
Project Period (FY) 1987 – 1988
Project Status Completed (Fiscal Year 1988)
Budget Amount *help
¥4,200,000 (Direct Cost: ¥4,200,000)
Fiscal Year 1988: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1987: ¥3,600,000 (Direct Cost: ¥3,600,000)
KeywordsLimonene / Prostaglandin / Rhodium (I) complex / Carbacyclin / 立体選択的閉環反応
Research Abstract

The results of this project were as follows:
1) Chemical conversion of (+)-limonene to prostaglandin (PG) E_2 could be almost established on the basis of stereoselective RH(I)-catalysed cyclization.
2) Carbacyclin was synthesized from (+)-limonen-10-ol by using RH(I)-catalysed cyclization, regioselective aldol condensation, and diastereoselective 1,4-addidion.
3) PGE_1 was synthesized by the new route on the basis of air-oxidation of cyclopentenones, chiral induction by microbial reduction, and diastereo- and chemo-selective conversion.
4) New ring conversion under acetalization condition, which was found in this project, was clarified to be effective for conversion from five membered ring to five ro six membered ring.

Report

(2 results)
  • 1988 Annual Research Report   Final Research Report Summary
  • Research Products

    (16 results)

All Other

All Publications (16 results)

  • [Publications] Z.-F.Xie: Chem.Pharm.Bull.35. 1812-1816 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] H.Suemune: Tetrahedron Lett.28. 3373-3376 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] K.Sakai: J.Synthetic Org.Chem.,Japan. 46. 334-343 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] H.Suemune: Chem.Pharm.Bull.36. 15-21 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] K.Okano: Chem.Pharm.Bull.,(B-4709).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] M.Hizuka: Chem.Pharm.Bull.,(B-4428).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Z.-F. Xie: "Conversion of (+)-Limonen-10-ol to Bicyclo[3.3.0]octane Skelton" Chem. Pharm. Bull.35. 1812-1816 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] H. Suemune: "Reconstruction of Five and Six Membered Ring" Tetrahedron Lett.28. 3373-3376 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] K. Sakai: "Synthesis of Biologically Active Compounds from Limonene" J. Synthetic Org. Chem., Japan. 46. 334-343 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] H. Suemune: "Enzymatic Procedure for the Synthesis of Prostaglandin A_2" Chem. Pharm. Bull.36. 15-21 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] K. Okano: "Preparation of Chiral Highly Functionallized Cyclopentanes and Its Application to the Synthesis of Prostaglandin E_1" Chem. Pharm. Bull., in press (B-4709).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] M. Hizuka: "A Stereocontrolled Synthesis of Trisubstituted Cyclohexanes and Cyclopentanes. Its Application to the Synthesis of 11-Deoxyprostaglandins" Chem. Pharm. Bull., in press (B-4428).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] K.Sakai: J.Synthetic Org.Chem.,Japan. 46. 334-343 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] H.Suemune: Chem.Pharm.Bull.36. 15-21 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] K.Okano: Chem.Pharm.Bull.(Bー4709).

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Hizuka: Chem.Pharm.Bull.(Bー4428).

    • Related Report
      1988 Annual Research Report

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Published: 1987-04-01   Modified: 2016-04-21  

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