A convenient resolution of racemic lavandulol through lipase-catalyzed acylation with succinic anhydride: simple preparation of enantiomerically pure (R)-lavandulol

(R)- and (S)-lavandulol and their esters are important compounds in perfumery and have recently become significant in pheromone research. (R)-Lavandulol and its esters, as well as the esters of (S)-lavandulol have been identified as sex and aggregation pheromones in two mealybugs, in thrips and in weevils. We report a convenient resolution of racemic lavandulol through lipase-catalyzed acylation with succinic anhydride. This method does not require tedious chromatographic separation and is particularly suitable for the preparation of enantiomerically pure (R)-lavandulol with 98% ee in one resolution cycle. The (S)-lavandulol with 90% ee can be obtained by a second resolution cycle.

Figure optionsDownload as PowerPoint slide

(R)-LavandulolC10H18OEe = 98%[α]D27=-11.1 (c 2.28, MeOH)Source of chirality: enzymatic resolution by acylation with succinic anhydrideAbsolute configuration: (R)