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

Abstract

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.