M. Barrot, G. Fabriàs, F. Camps
1994
Citations
0
Influential Citations
16
Citations
Journal
Tetrahedron
Abstract
Abstract The synthesis of deuterium labeled 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- 2 H 3 ] 11-hexadecynoic acid, deuterium atoms were introduced by reaction of iodoalkyne 6b with (CD 3 ) 2 CuLi. Alkylation of terminal diyne 14b with CD 3 CD 2 I followed by stereoselective reduction of the corresponding diyne to the corresponding (Z,Z) diene afforded [15,15,16,16, 16- 2 H 5 ] (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.