Asymmetric synthesis of methyl (-)-13-oxo-15,16-dinorlabda-8(17),11E-dien-19-oate, methyl ester of a potent suppressor toward carcinogenic promotor.
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.
Katoh
Takahiro
T
Department of Pharmaceutical Manufacturing Chemistry, 21st Century COE Program, Kyoto Pharmaceutical University, Misasagi, Kyoto 607-8412, Japan.
Mizumoto
Shinsuke
S
Fudesaka
Masato
M
Kajimoto
Tetsuya
T
Node
Manabu
M
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016588:Anticarcinogenic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008968:Molecular Conformation; D011401:Promoter Regions, Genetic / Q000187:drug effects*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D029783:Thuja / Q000737:chemistry
C514042:1,4a-dimethyl-5-oxodecahydronaphthalene-1-carboxylate; D000475:Alkenes; D016588:Anticarcinogenic Agents; D004224:Diterpenes; C514041:methyl-13-oxo-15,16-dinorlabda-8(17),11E-dien-19-oate