Enzymatic transesterification of racemic lavandulol: preparation of the two enantiomeric alcohols and of the two enantiomers of lavandulyl senecioate

Abstract

( R) and ( S)-lavandulol are important compounds in the cosmetics industry and in pheromone research. The senecioyl ester of ( S)-lavandulyl has recently been identified as the sex pheromone of the vine mealybug, a significant pest in vineyards. We herein report the preparation of the two enantiomers of lavandulol and lavandulyl senecioate, starting from racemic lavandulol. The preparation is based on a two-cycle enzymatic transesterification of racemic lavandulol with vinyl acetate using Porcine pancreas lipase. High enantioselectivity was achieved while the preparation yielded ( R)-lavandulol with 96.7% ee and ( S)-lavandulol with 92.6% ee.