Synthesis of versatile chiral intermediate for drimane sesquiterpenes and labdane diterpenes based on enzymatic resolution

The lipase PL-266 from Alcaligenes sp. catalyzed enantioselective acetylation of the decahydro-5,5,8a-trimethyl-2-oxo-naphthalene-1-methanol-2-ethylene acetal (±)-6 was carried out and an acetate (8aS)-7 and an alcohol (8aR)-6 possessing high enantiomeric excess (>98% ee), respectively, were obtained. Both (8aS)-7 and (8aR)-6 were converted to the (8aS)- and (8aR)-decahydro-5,5,8a-trimethyl-2-oxo-naphthalene-1-carboxylates (4), respectively. The (8aR)-β-keto ester (4) was converted to the important intermediate (8aR)-16 for the synthesis of natural hyatellaquinone (3).