Asymmetric Synthesis of Methyl (-)-13-Oxo-15,16-dinorlabda-8(17),11E-dien-19-oate, Methyl Ester of a Potent Suppressor toward Carcinogenic Promotor

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  • Katoh Takahiro
    Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University
  • Mizumoto Shinsuke
    Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University
  • Fudesaka Masato
    Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University
  • Kajimoto Tetsuya
    Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University
  • Node Manabu
    Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University

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Asymmetric synthesis of methyl ester (4) of (−)-13-oxo-15,16-dinorlabda-8(17),11E-dien-19-oic acid (1), which exhibited the most potent activity for the prevention of incipient carcinogenesis among the isolated diterpenes from Thuja standishii and its related plants, was achieved by using methyl (−)-1,4a-dimethyl-5-oxodecahydronaphthalene-1-carboxylate (5) as a strating material, which was easily prepared on gram scale by baker's yeast-catalyzed asymmetric reduction.

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