Department of Entomology, University of California, Riverside CA-92521, USA.
Diastereoisomeric (Z)-(1R,2S,4S)- and (Z)-(1S,2R,4S)- epoxybisabolenes, sex pheromone components of the stink bugs Nezara viridula and Acrosternum hilare were synthesized stereoselectively in three steps from commercially available (-)-limonene oxide. Two other stereoisomers, (E)-(1R,2S,4S)- and (E)-(1S,2R,4S)- epoxybisabolenes were obtained in two steps from the same starting material. The other 4 stereoisomers also are accessible simply by substituting (+)-limonene oxide for (-)-limonene oxide, providing short, stereoselective routes to all eight possible stereoisomers.