Enzymatic resolution of cis- and trans-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxo-naphthyl acetate derivatives

Article abstract of DOI:10.1016/S0957-4166(02)00551-7

Extensive screenings using commercially available enzymes were performed in relation to the asymmetric hydrolysis reactions of the (±)-cis- (1, 3 and 5) and (±)-trans-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxo-naphthyl acetates (7, 9 and 11). The combinations of enzymes from plants and cis-equatorial compounds as well as the combinations of lipases from microorganisms and trans-axial-5-methoxycarbonyl acetate showed high enantiomeric ratio in asymmetric hydrolysis. However, the enantiomeric ratio of the combinations of lipases from microorganisms and trans-axial isomers except trans-axial-5-methoxycarbonyl derivative was less satisfactory. High E values (>200) were observed when β-amylase from wheat and lipase from Candida cylindracea were used for the (±)-cis-acetate 1 and the (±)-trans-isomer 7, respectively, to obtain the corresponding chiral products with high enantiomeric ratios (>99:1).