A convenient synthesis of (2s,3r,6s,7z)- and (2r,3s,6s,7z)-2,3-epoxy- 7,10-bisaboladiene, the sex pheromones of the southern green stink bug (nezara viridula)

Article abstract of DOI:10.1016/S0040-4020(98)00696-6

(2S,3R,6S,7Z)-2,3-Epoxy-7,10-bisaboladiene, a sex pheromone component of the southern green stink bug, Nezara viridula (L.) was synthesized stereoselectively in four steps (19% overall yield) from (S)-4-methyl-3- cyclohexene-1-carboxylic acid. This epoxy bisaboladiene was converted in three more steps (64% yield) to its (2R,3S,6S,7Z)-isomer, another sex pheromone component of the southern green stink bug, by inverting the configuration of the epoxide ring.