Abstract

A practical and scalable synthesis of (Z)-9-tricosene, the sex pheromone of the housefly, has been achieved by the addition of one-carbon unit from the readily available (Z)-erucic acid. The synthesis is composed of three consecutive steps, lithium aluminium hydride reduction of erucic acid, tosylation of the resulting alcohol, and copper-catalyzed Kumada- type cross-coupling of the tosylate with methylmagnesium bromide as the key step. This approach is quite straightforward and capable of scale-up synthesis.

Keywords: (Z)-9-Tricosene, biochemical pesticide, erucic acid, housefly, kumada cross-coupling, sex pheromone, conventional pesticides, muscalure, straightforward, Grignard addition