A Modified Thermodynamically Controlled Deracemization of 2-Allylcyclohexanone and Its Application to Asymmetric Synthesis of (R)-(-)-Epilachnene

The efficiency of thermodynamically controlled deracemization was influenced considerably by the solvent used. Based on this finding, an improved method was developed, by which 2-allylcyclohexanone was converted to the R-isomer of 93% ee in 72% yield. As an application of the method, (R)-(-)-epilachnene, an antipode of the defensive droplets from the Mexican bean beetle, Epilachna varivestis, was synthesized in short steps.