Enantioselectivity of Microbial Hydrolysis of (+/-)-Decahydro-2-naphthyl Acetates. Preparation and Absolute Configurations of Chiral Decahydro-2-naphthols

Article abstract of DOI:10.1021/jo00194a004

Absolute configurations of chiral decahydro-2-naphthols, which were obtained by microbial hydrolysis of corresponding (+/-)-acetates and chloroacetates, were elucidated by chemical correlation to (4aS,8aS)-trans-octahydro-2(1H)-naphthalenone (5).Decarboxylation of the (-)-α-methylbenzylamine salt of (-)-2-oxo-2,3,4,4a,5,6,7,8-octahydro-4a-naphthalenecarboxylic acid (1a) gave (+)-(S)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone (3), which was reduced with lithium in liquid ammonia to (+)-(4aS,8aS)-trans-octahydro-2(1H)-naphthalenone (5).Catalytic hydrogenation of (-)-3gave (-)-(4aR,8aS)-cis-octahydro-2(1H)-naphthalenone (4), which was already obtained by oxidation of (-)-cis,cis-decahydro-2-naphthol (7) with chromic acid.These results mean that (-)-7 has the 2S,4aR,8aS configuration.Furthermore, the absolute configuration of (-)-7 was confirmed by X-ray analysis of its p-bromobenzoate.