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1991 Fiscal Year Final Research Report Summary

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
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.

  • Research Products

    (12 results)

All Other

All Publications (12 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 1993-03-16  

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