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
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