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Novel Ring Transformation Reaction

Research Project

Project/Area Number 02453142
Research Category

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

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

Principal Investigator

SAKAI Kiyoshi  Kyushu Univ., Pharmaceutical Sciences, Professor, 薬学部, 教授 (90153840)

Co-Investigator(Kenkyū-buntansha) SUEMUNE Hiroshi  Kyushu Univ., Pharmaceutical Sciences, Assistant Professor, 薬学部, 助手 (20095897)
FUNAKOSHI Kazuhisa  Kyushu Univ., Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (50037579)
Project Period (FY) 1990 – 1991
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥4,600,000 (Direct Cost: ¥4,600,000)
Fiscal Year 1991: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1990: ¥3,800,000 (Direct Cost: ¥3,800,000)
Keywordsring transformation / aldol condensation / acetalization / Grob fragmentation / boron trifluoride / ring cleavage / ethylene glycol
Research Abstract

A novel ring transformation reaction based on aldol condensation followed by acetafization and subsequent Grob fragmentation has been developed by our group. This reaction takes place when the cychc ketones with a carbonyl function at the side chain are subjected to acetatization using BF_3/ethylene glycol in CH_2Cl_2 at room temperature. This facile ring transformation can be classified into two types. One is the intramolecular ring transformation, and the other is the intermolecular ring transformation. The intramolecular ring transformation reaction has been successfully applied for the synthesis of natural products such as bulnesol, acorenone B, trichodiene, and phoracantholide 1. The reaction based on intermolecular aldol condensation has provided a novel synthetic route to chiral straight-chain compounds with syndiotactic methyl function. Ring transformation from readily prepared bicycle[3.3.0]octan-3-ones to bicycle[3.2.1]oct-2-ones is now extended to a study of asymmetric ring transformation.

Report

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

    (20 results)

All Other

All Publications (20 results)

  • [Publications] Takayosi Yamamoto: "Novel Skeketal Transformation of Bicyclo〔3.3.0〕octanones to Bicyclo〔3.2.1〕octenes" Tetrahedron Letters. 32. 515-516 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Takayoshi Yamamoto: "An Insight into the Novel Ring Transformation Reactions Using Ethylene Glycol/BF_3" Tetrahedron. 47. 8523-8528 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masakazu Tanaka: "Synthesis of (dl)-Trichodiene Using Novel Ring Transformation Reaction" Tetrahedron Letters. 32. 5581-5584 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Shinji Nagumo: "Synthesis of Phoracantholide I Based on Stereospesific Fragmentation Reactions" Tetrahedron Letters. 32. 5585-5588 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Aki Matsukuma: "Preparation of Chiral Straight-chain Compounds with Syndiotactic Methyl Function" Tetrahedron Letters. 32. 7559-7562 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Shinji Nagumo: "Ring Cleavage Reaction Based on Intermolecular Aldol Condensation" J.Chem.Soc.,Chem.Commun.1538-1539 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] S. Nagumo, A. Matsukuma, F. Inoue, T. Yamamoto, H. Suemune and K. Sakai: "Ring Cleavage Reaction Based on Intermolecular Aldol Condensation" J. Chem. Soc., Chem common.1538-1539 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] T. Yamamoto, T. Eki, S. Nagumo, H. Suemune and K. Sakai: "Novel Skeletal Transformation of Bicycle[3.3.0]octanones to Bicycle[3.2.1]octanes" Tetrahedron Lett.32. 515-516 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] M. Tanaka and K. Sakai: "Synthesis of (dl)-Trichodiene Using Novel Ring Transformation Reaction" Tetrahedron Lett.32. 5581-5584 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] S. Nagumo, H. Suemune and K. Sakai: "Synthesis of Phoracantholide I Based on Stereospecific Fragmentation Reactions" Tetrahedron Lett.32. 5585-5588 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] T. Yamamoto, H. Suemune and K. Sakai: "An Insight into the Novel Ring Transformation Reactions Using Ethylene Glycol/BF3" Tetrahedron. 47. 8523-8528 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] A. Matsukuma, S. Nagumo, H. Suemune and K. Sakai: "Preparation of Chiral Straight-chain Compounds with Syndiotactic Methyl Function" Tetrahedron Lett.32. 7559-7562 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Takayosi Yamamoto: "Novel Skeketal Transformation of Bicyclo[3.3.0]octanones to Bicyclo[3.2.1]octenes" Tetrahedron Letters. 32. 515-516 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Takayoshi Yamamoto: "An Insight into the Novel Ring Transformation Reactions Using Ethylene Glycol/BF_3" Tetrahedron. 47. 8523-8528 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Masakazu Tanaka: "Synthesis of(dl)ーTrichodiene Using Novel Ring Transformation Reaction" Tetrahedron Letters. 32. 5581-5584 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Shinji Nagumo: "Synthesis of Phoracantholide I Based on Stereospesific Fragmentation Reactions" Tetrahedron Letters. 32. 5585-5588 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Aki Matsukuma: "Preparation of Chiral Straightーchain Compounds with Syndiotactic Methyl Function" Tetrahedron Letters. 32. 7559-7562 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Shinji Nagumo: "Ring Cleavage Reaction based on Intermolecular Aldol Condensation" J.Chem.Soc.,Chem.Commun.1538-1539 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Shinji Nagumo: "Stereocontrolled Synthesis of (±)ーAcorenone B based on New Ring Conversion" J.Chem.Soc.,Chem.Commun.1778-1779 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Takayoshi Yamamoto: "Novel Skeletal Transformation of Bicyclo[3.3.0]octanones to Bicyclo[3.2.1]octenes" Tetrahedron Letters. 32. 515-516 (1991)

    • Related Report
      1990 Annual Research Report

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

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