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Synthesis of anti-viral Carbocyclic Nucleosides by Stereosclective Control of Cycloaddition Reactions.

Research Project

Project/Area Number06651012
Research Category

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

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKagoshima University

Principal Investigator

SOMEKAWA Kenichi  Kagoshima Univ., Fac.of Eng., Professor, 工学部, 教授 (10041534)

Co-Investigator(Kenkyū-buntansha) UEMURA Hisako  Kagoshima Univ., Fac.of Eng., Research Assoc., 工学部, 助手 (20041535)
SHIMO Tetsuro  Kagoshima Univ., Fac.of Eng., Associate Prof, 工学部, 助教授 (80041565)
村岡 富美子  鹿児島大学, 工学部, 教務職員 (90229948)
Project Period (FY) 1994 – 1995
Project Status Completed(Fiscal Year 1995)
Budget Amount *help
¥1,300,000 (Direct Cost : ¥1,300,000)
Fiscal Year 1995 : ¥500,000 (Direct Cost : ¥500,000)
Fiscal Year 1994 : ¥800,000 (Direct Cost : ¥800,000)
KeywordsHIV / Anti-virnus / Photocycloaddition / C-nucleosides / Carbocyclic-Oxetanocins / 炭素環ヌクレオシド / 抗ウイルス
Research Abstract

Some carbocyclic oxetanocins exibit wide antiviral and potent anti-HIV activities. Several synthetic methods for the oxetanocins have been reported. Such studies are quite important as a scientific challenge against AIDS.
We have describe improved and facile methods to synthesize a chiral exetanocin and the analogues by way of much shortened routes employing photocycloadditions of maleic anhydrides with vinyl acetate as the key-step reactions.
An endo-[2+2]cycloadduct prepared by the photoreaction was derived to some chiral cyclobutan-dicarboxylates and coupled with adenine to give carbocyclic oxetanocins, but the mothods was not effective for the optical ones. An adenine-cyclobutane-dicarboxylate was optically resolved using a chiral acid and is being subjected for reduction to give a chiral carbocyclic oxetanocin.
The oxetanocin analogues were derived via photoreactions of methylmaleic anhydride with vinyl acetate. The reactions are also effective for mechanistic analysis of the coupling and reduction reactions.
On the other hand, many photocycloaddition reactions between two different type of molecules were investigated in non-solution systems and the factors for steric selectivity on the [2+2]cycloadditions were analyzed, and it was inferred that some ground state interactions between the two molecules influenced to the steric selectivity.

Report

(3results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report

Research Products

(12results)

All Other

All Publications

  • [Publications] Kenichi Somekawa: "Synthesis of a Carbocyclic Oxetanocin Using Photocycloaddition" Chemistry Letters. 1995. 407-408 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Tetsuro Shimo: "Intramolecular Photoreactions of 6-(ω-Alkenyl)-4-methoxy-2-pyrones" J. Heterocyclic Chem. 31. 387-390 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Tetsuro Shimo: "Synthesis of 9-Oxa-5-azatricyclo [4.3.0.0.^<3,7>] nonan-4-ones from 4,4,5 Trihydroxy-2-oxabicyclo [3.2.0] heptane-exo-6-carbonitriles by Their Ring Transformation" Bull. Chem. Soc. Jpn.67. 2891-2893 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Tetsuro Shimo: "Photochemical Behavior of 4-(ω-Enyl)-and 4-(ω-Dienyl)-s-pyrones" J. Heterocyclic Chem.32. 341-345 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Tetsuro Shimo: "Intramolecular Photocycloadditions of 6,6'-Dimethyl-4,4'-polymethylenedioxy-di-2-pyrones" J. Heterocyclic Chem.32. 727-730 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Kenichi Somekawa: "Synthesis of a Carbocyclic Oxetanocin Using Photocycloaddition" Chemistry Letters. 1995. 407-408 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] T.Shimo, S.Matsuzaki, K.Somekawa: "Intramolecular Photoreactions of 6- (omega-Alkenyl) -4-methoxy-2-pyrones" J.Heterocyclic Chem. 31. 387-390 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] T.Shimo, K.Ohshima, K.Somekawa, M.Kawaminami: "Synthesis of 9-Oxa-5-azatricyclo [4.3.0.0.^<3,7>] nonan-4-ones from 4,4,5 Trihydroxy-2-oxabicyclo [3.2.0] heptane-exo-6-carbonitriles by Their Ring Transformation" Bull.Chem.Soc.Jpn.67. 2891-2893 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] T.Shimo, S.Ueda, K.Somekawa: "Photochemical Behavior of 4- (omega-Enyl) -and 4- (omega-Dienyl) -2-pyrones" J.Heterocyclic Chem.32. 341-345 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] T.Shimo, S.Ueda, T.Suishu, K.Somekawa: "Intramolecular Photocycloadditions of 6,6'-Dimethyl-4,4'-polymethylenedioxy-di-2-pyrones" J.Heterocyclic Chem.32. 727-730 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] K.Somekawa, R.Hara, K.Kinnami, F.Muraoka, T.Suishu, T.Shimo: "Synthesis of a Carbocyclic Oxetanocin Using Photocycloaddition" Chemistry Letters., 1995. 407-408 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 染川賢一: "Synthesis of a Carbocyclic Oxetanocin Using Photocycloaddition" Chemistry Letters. 1995. 407-408 (1995)

    • Related Report
      1995 Annual Research Report

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Published : 1994-04-01   Modified : 2016-04-21  

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