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SYNTHESIS OF BIOLOGICALLY ACTIVE COMPOUNDS FROM LIMONENE

Research Project

Project/Area Number 63570995
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKYUSHU UNIVERSITY

Principal Investigator

SAKAI Kiyoshi  KYUSHU UNIV., FACULTY OF PHARMACEUTICAL SCIENCES, PROFESSOR, 薬学部, 教授 (90153840)

Co-Investigator(Kenkyū-buntansha) FUNAKOSHI Kazuhisa  KYUSHU UNIV. FACULTY OF PHARMACEUTICAL SCIENCES, ASSISTANT PROFESSOR, 薬学部, 助手 (50037579)
SUEMUNE Hiroshi  KYUSHU UNIV., FACULTY OF PHARMACEUTICAL SCIENCES, ASSISTANT PROFESSOR, 薬学部, 助手 (20095897)
Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1989: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1988: ¥1,800,000 (Direct Cost: ¥1,800,000)
Keywordslimonene / prostaglandin / rhodium (I) complex / stereoselective cyclization / リモーネン
Research Abstract

1. Synthesis of PGE_2 from Limonene Synthesis of PGE_2 has been achieved by using the chirality of limonene. But, the chemical yield of the last step was low. The enhancement of the yield is now under investigation.
2. New synthetic route to prostaglandins a) New synthetic route to alpha,beta-unsaturated gamma-lactone has been developed. Stereoselective 1,4-addition to the gamma-lactone, and subsequent intramolecular alkylation afforded bicyclic system, which could be easily converted to 11-deoxyprostaglandins intermediate. b) Highly functionalized cyclopentenone, which was promised to be useful as chiral synthon, was synthesized by air oxidation and subsequent microbial reduction. By using this compound, new synthetic route to PGE_1 has been developed.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [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(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Hizuka: "A Stereocontrolled Synthesis of Trisubstituted Cyclo-hexanes and Cyclopantanes.Its Applications to the Synthesis of 11-Deoxyprostaglandins." Chem.Pharm.Bull.37. 1185-1187 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H.Suemune: "Preparation of Optically Active γ-Hydroxymethyl α,β-Unsaturated γ-Lactone Using an Enzymatic Procedure." Chem.Pharm.Bull.37. 1379-1381 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] K.Okano: "Preparation of Chiral,Highly Functionalized Cyclo-pentanes and Its Application to the Synthesis of Prostaglandin E_l." Chem.Pharm.Bull.37. 1995-1998 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiyoshi Sakai and Hiroshi Suemune: "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
      1989 Final Research Report Summary
  • [Publications] Michiyo Hizuka, Chenglin Fang, Hiroshi Suemune, and Kiyoshi Sakai: "A Stereocontrolled Synthesis of Trisubstituted Cyclohexanes and Cyclopentanes." Chem. Pharm. Bull., 37, 1185-1187, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Hiroshi Suemune, Michiyo Hizuka, Tomoko Kamashita, and Kiyoshi Sakai: "Preparation of Optically Active gamma-Hydroxy-alpha, beta-Unsaturated gamma-Lactone Using an Enzymatic Procedure." Chem. Pharm. Bull., 37, 1379-1381, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Koji Okano, Hiroshi Suemune, and Kiyoshi Sakai: "Preparation of Chiral Highly Functionalized Cyclopentanes and Its Applications to the Synthesis of Prostaglandin E_1." Chem. Pharm. Bull., 37, 1995-1998, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H.Suemune: "Preparation of Optically Active γ-Hydroxymethl α,β-Unsaturated γ-Lactone Using an Enzymatic Procedure." Chem.Pharm.Bull.37. 1379-1381 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Hizuka: "A Stereocontrolled Synthesis of Trisubstituted Cyclohexanes and Cyclopentanes.Its Application to the Synthesis of 11ーDeoxyprostaglandins." Chem.Pharm.Bull.37. 1185-1187 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] K.Okano: "Preparation of Chiral,Highly Functionalized Cyclopentanes and Its Application to the Synthesis of Prostaglandin E_1." Chem.Pharm.Bull.37. 1995-1998 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] K.Sakai.: J.Synthetic Org.Chem.,Japan. 46. 334-343 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] K.Okano.: Chem.Pharm.Bull.,.

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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