A simple synthesis of 4E,7Z-tridecadien-1-yl acetate, a component of the sex pheromone of the potato moth Phtorimaea operculella (Lepidoptera: Gelehiidae)

Article abstract of DOI:10.1007/BF01430748

A simple, five-step synthesis of the title compound was developed starting from commercially available 2,4-nonadienal. The overall yield of the pheromone is 29%, and the geometric purity of the Δ⁴ and Δ⁷ double bonds is ≥95%. The Z configuration of the Δ⁷ bond results from the 1,4-cis-hydrogenation of the intermediate 1,4,6-undecatrien-3-ol in the presence of an (arene)chromium tricarbonyl complex, while the E configuration of the Δ⁴ bond arises in the Claisen-Johnson rearrangement occuring in the reaction of 1,5Z-undecadien-3-ol with trimethyl orthoacetate.