Lipase behavior in the stereoselective transesterification of zingerol-like derivatives and related biphenyls

Using a highly stereoselective enzymatic procedure based on the irreversible transesterification of alcoholic functions in organic solvent, both enantiomers of zingerol and dehydrozingerol . O-methyl derivatives . 1 and . 2 were obtained in high optical purity. The biocatalytic method was then extended to the corresponding biphenyl derivatives . 5-8 for which an one-pot resolution/desymmetrization was carried out on the whole racemic/. meso mixtures to give single stereoisomers with very high enantiomeric and diastereoisomeric excesses. The comparison of kinetic and enantioselective behavior of the lipase AK from . Pseudomonas fluorescens in the transesterification of monomer (±)-. 1 and the related (±)-. 5 and meso-. 6 biphenyl dimers was also made.