Asymmetric synthesis of sex pheromone of the western hemlock looper, Lambdina fiscellaria lugubrosa (Hulst)

Abstract

The western hemlock looper is an economically important defoliator of coniferous trees. Its sex pheromone has been synthesized in 36–50% total yield using the enantiomers of 2-methyloxiraneoxide as chiral sources. The key steps of this strategy involved CuI catalyzed ring-opening of chiral 2-methyloxiraneoxide, stereospecific inversion of secondary tosylate and Wittig coupling of the aldehyde with chiral phosphonium salt. The synthetic pheromones would be used to monitor and control this pest.