Synthesis of the enantiomers of (3Z,9Z)-cis-6,7-epoxy-3,9-octadecadiene, one of the major components of the sex pheromone of Ectropis oblique Prout

Abstract Both enantiomers of (3 Z ,9 Z )- cis -6,7-epoxy-3,9-octadecadiene, one of which is the major component of the sex pheromone of Ectropis oblique Prout, were synthesized in 23% overall yield for the (−)-(6 S ,7 R )-enantiomer and 18% yield for the (+)-(6 R ,7 S )-isomer. This protocol uses a sequential regioselective ring-opening strategy and provides a convenient and reliable access to other structurally related insect sex pheromones. Preliminary biological studies revealed that (−)-(6 S ,7 R )- 2a was roughly as active as the natural pheromone, while racemic (±)- 2 was less bioactive and (+)- 2b was much less bioactive.