Synthesis of (Z,Z)-11,13-Hexadecadienal, a Principal Component of Navel Orangeworm (Pamyelois transitella) Pheromone

Article abstract of DOI:10.1021/jo00153a007

This report outlines a commercial synthetic process for (Z,Z)-11,13-hexadecadienal (navel orangeworm pheromone).The synthetic scheme which is employed introduces the stereochemically labile conjugated diene moiety at a late stage in the synthesis, thereby avoiding complications during the purification of intermediates.In addition, the aldehyde function is generated through a Grignard reaction sequence, obviating the generally accepted techniques which are usually unsuitable for commercial preparations.We have also observed the first reported selective inclusion by urea of a conjugated (Z,Z)-diene as a means of mild purification of labile dienic pheromone intermediates.