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

[Display omitted] 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.