Efficient and practical synthesis of both enantiomers of 3-phenylcyclopentanol derivatives

An efficient, multigram scale synthesis of the respective optical isomers of 3-(substituted-phenyl) cyclopentanols was achieved by a lipase-catalyzed transesterification (kinetic resolution) in organic medium. This enzymatic reaction proceeded with great efficiency as measured by chemical yield and enantioselectivity. The racemic cis-alcohol was successfully resolved to yield (1R,3S)-acetate and the corresponding (1S,3R)-alcohol . The utility of this procedure was demonstrated by the practical syntheses of the biologically active compounds. The (1R,3S)-acetate and the (1S,3R)-alcohol were converted into orally active 5-lipoxygenase inhibitors, respectively, without loss of optical purity.