Synthesis of the Sex Pheromones of the Pine Caterpillar, Dendrolimus punctatus (Walker)

The pine caterpillar, Dendrolimus punctatus (Walker), is a notorious forest pest. An efficient and convenient synthesis of the sex pheromones of this pest has been achieved. In our synthetic approach, a Wittig coupling of an aldehyde with an ester-bearing phosphonium salt was used to construct the Z-alkene, whereas the E-alkene was prepared via a stereoselective reduction of an alkyne with LiAlH4. The synthetic sex pheromones would be useful for integrated pest management of the pine caterpillar.