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
Jie Yu†, Feng Guo†, Yun-Qiu Yang, Hui-Hui Gao, Ru-Yan Hou, Xiao-Chun Wan*
Tetrahedron: Asymmetry, https://doi.org/10.1016/j.tetasy.2017.04.010
Both enantiomers of (3Z, 9Z)-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 (−)-(6S, 7R)-enantiomer and 18% yield for the (+)-(6R, 7S)-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 (−)-(6S, 7R)-2a was roughly as active as the natural pheromone, while racemic (±)-2 was less bioactive and (+)-2b was much less bioactive.