Synthesis of 11-Hexadecynoic Acid and (Z,Z)-11,13-Hexadecadienoic Acid and their use as Tracers in a Key Step of the Sex Pheromone Biosynthesis of the Processionary Moth.

Article abstract of DOI:10.1016/S0040-4020(01)85545-9

The synthesis of deuterium labelled 11-hexadecynoic acid and (Z,Z)-11,13-hexadecadienoic acid and their use to investigate the biosynthetic pathway of the processionary moth sex pheromone is reported.In <16,16,16-2H3> 11-hexadecynoic acid, deuterium atoms were introduced by reaction of iodoalkyne 6b with (CD3)2CuLi.Alkylation of terminal diyne 14b with CD3CD2I followed by stereoselective reduction of the corresponding diyne to the corresponding (Z,Z) diene afforded <15,15,16,16,16-2H5>(Z,Z)-11,13-hexadecadienoic acid.GLC-MS analyses of extracts from pheromone glands incubated with these tracers revealed that the acetylenic acid, but not the dienoic acid, is a precursor of the pheromone enyne system.