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Stereoselective Cyclization Reactions Using Organotin Compounds

Research Project

Project/Area Number 63550616
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionChiba University, Faculty of Engineering

Principal Investigator

YAMAMOTO Makoto  Chiba Univ., Fac. Eng. (Ass. Professor), 工学部, 助教授 (50039294)

Co-Investigator(Kenkyū-buntansha) KOHMOTO Shigeo  Chiba Univ., Fac. Eng. (Assistant), 工学部, 助手 (90195686)
YAMADA Kazutoshi  Chiba Univ., Fac. Eng. (Professor), 工学部, 教授 (60009230)
Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 1989: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1988: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsOrganotin Compound / LTA Cyclization / Radical Cyclization / Epoxy-allylic Tin Compound / Thionolactone Synthesis / Stereoselective Cyclization / Tandem Cyclization / 立体選択的環化反応
Research Abstract

The following results were obtained from the study of "Stereoselective Cyclisation Reactions Using Organotin Compounds".
1). By the oxidative substitution reactions of organotin compounds with LTA gave corresponding oxygen-functionalized one. This oxidation was applied to the synthesis of 4-ylidenebutenolides. Treatment of 5-stannyl-1,3-pentandiol derivatives with LTA gave 4-hydroxytetrahydropyran in good yield. The diol which has a double or a triple bonds in its molecule were further cyclized to a polycyclic ether. The cyclization of 3-hydroxy-5-stannyl- pentanoic acid yielded 4-hydroxy-delta-lactone.
2). The radical cyclization of xanthates using tri-n-butyltin hydride gave a thionolactone which was easily oxidized to its lactone. The diastereo- selectivity of the cyclization was well controlled (de> 95%). The linear xanthates having two kinds of radical acceptor sites also cyclized to multifused thionolactone (Tandem radical cyclization).
3). Lewis-acid induced regio- and stereoselective cyclization of epoxy-allylic stannanes was also carried out. The cyclization proceeded in good yield, and the regioselectivity of the cyclization was governed by the stability of the carbocation which was formed. The stereochemistry around the epoxide carbons was also discussed.

Report

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

    (29 results)

All Other

All Publications (29 results)

  • [Publications] M.Yamamoto: "Oxidative Substitution Reactions of Organotin Compounds with Lead Tetraacetate" J.Chem.Soc.,Chem.Commun.,. 1988. 560-561 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 山本忠: "有機スズ化合物のトランスメタル化を経由する有機合成-位置および立体選択的合成-" 有機合成化学協会誌. 46. 1134-1148 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Yamamoto: "Oxidative Substitution Reactions of Olefinic Tin Compounds with Lead Tetra-acetate" Chem.Lett.,. 1989. 221-222 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 山本忠: "4-アルキリデンブテノリド類の位置選択的合成法" 日本化学会誌. 1989. 760-763 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Yamamoto: "Tri-n-butyltin Hydride Assisted Highly Stereoselective Lactonisation of Homoallylic Xanthates" J.Chem.Soc.,Chem.Commun.,. 1989. 1265-1266 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Yoshitake: "Lewis-Acid Induced Regio-and Stereoselective Cyclisation of Epoxy-allylic Stannanes" J.Chem.Soc.,Perkin Commun.,.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] S.Iwasa: "Synthesis of Thionolactones from Homoallylic Xanthates" J.Org.Chem.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Yamamoto: "Intramolecular Oxidative Cyclization of 5-Stanny1-1,3-pentanediol Derivatives with Lead Tetra-acetate" J.Chem.Soc.,Chem.Commun.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Yamamoto: "Oxidative Substitution Reactions of Organotin Compounds with Lead Tetra-acetate.A Novel Route to 4-Ylidene-butenolides" J.Chem.Soc.,Perkin Trans I.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Yamamoto, H. Izukawa, M. Saiki, and K. Yamada: "Oxidative Substitution Reactions of Organotin Compounds with Lead Tetra-acetate" J. Chem. Soc., Chem. Commun., 1988, 560-561.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Yamamoto, S. Kohmoto and K. Yamada: "Organic Synthesis through the Transmetallation Reaction of Organotin Compounds. Regio- and Stereoselective Synthesis" J. Synth. Org. Chem. Japan, 46, 1134-1148(1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Yamamoto, S. Irie, M. Miyashita, S. Kohmoto and K. Yamada: "Oxidative Substitution Reaction of Olefinic Tin Compounds with Lead Tetraacetate" Chem. Lett., 1989, 221-222.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Yamamoto, T. Uruma, S. Kohmoto and K. Yamada: "Regioselective Synthesis of 4-Alkylidenbutenolides" Nippon Kagaku Kaishi, 1989, 760-763.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Yamamoto, T. Uruma, S. Iwasa, S. Kohmoto and K. Yamada: "Tri-n-butyltin Hydride Assisted Highly Stereoselective Lactonization of Homoallylic Xanthates" J. Chem. Soc., Chem. Commun., 1989, 1265-1266.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Yoshitake, M. Yamamoto, S. Kohmoto and K. Yamada: "Lewis Acid-Induced Regio- and Stereo-selective Cyclisation of Epoxy- allylic Stannane." J. Chem. Soc., Perkin Commun.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] S. Iwasa, M. Yamamoto, S. Kohmoto and K. Yamada: "Synthesis of Thionolactones from Homoallylic Xanthates" J. Org. Chem.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Yamamoto, S. Irie, T. Arase, S. Kohmoto and K. Yamada: "Intramolecular Oxidative Cyclisation of 5-Stannyl-1, 3-pentanediol Derivatives with Lead Tetra-actate" J. Chem. Soc., Chem. Commun.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Yamamoto, H. Munakata, S. Kohmoto and K. Yamada: "Oxidative Substitution Reactions of Organotin Compounds with Lead Tetra-acetate. A Novel Route to 4-Ylidenebutenolides" J. Chem. Soc., Perkin Trans I.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 山本忠: "4-アルキリデンブテノリド類の位置選択的合成法" 日本化学会誌. 1989. 760-763 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Yamamoto: "Tri-n-butyltin Hydride Assisted Highly Stereoselective Lactonisation of Homoallylic Xanthates" J.Chem. Soc.,Chem.Commun.,. 1989. 1265-1266 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Yoshitake: "Lewis-Acid Induced Regio-and Stereoselectice Cyclisation of Epoxy-allylic Stannanes" J.Chem.Soc.,Perkin Commun.,.

    • Related Report
      1989 Annual Research Report
  • [Publications] S.Iwasa: "Synthesis of Thionolactones from Homoallylic Xanthates" J.Org.Chem.,.

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Yamamoto: "Intramolecular Oxidative Cyclisation of 5-Stannyl-1,3-pentanediol Derivatives with Lead Tetra-acetate" J.Chem.Soc.,Chem.Commun.,.

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Yamamoto: "Oxidative Substitution Reactions of Organotin Compounds with Lead Tetra-acetate.A Novel Route to 4-Ylidene-butenolides" J.Chem.Soc.,Perkin Trans I.

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Yamamoto: J.Chem.Soc.,Chem.Commun.1988. 560-561 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Yamamoto: Chem.Lett.1989. 221-222 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] 山本忠: 有機合成化学協会誌. 46. 1134-1148 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Yamamoto: J.Org.Chem.

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Yamamoto: J.Org.Chem.

    • Related Report
      1988 Annual Research Report

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

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