A Novel Approach to the Synthesis of 7(Z), 11(Z)-Nonacosadiene, Pheromone of Drosophila Melano Gaster and 9(Z)-Tricosene, Pheromone of Musca Domestica

The synthesis of 7(Z), 11(Z)-Nonacosadiene (1), the pheromone1 of Drosophila melanogaster has been reported2 recently from a tetrahydrophyridine derivative involving a silicon induced fragmentation reaction as the crucial step. 9(Z)-Tricosene (2) also known as Muscalure and Muscanone is the biologically most active hydrocarbon, isolated from the extracts of cuticular and fecal lipids of sexually mature female houseflies, Musca Domestica. Several synthetic approaches3 for the synthesis of (2) have been reported in the literature. In this communication, we wish to report a novel synthetic approach for the pheromones (1) and (2), employing stepwise alkylation of N,N-dimethylacetone hydrazone (3) as the key step of the synthesis.