Practical and Scalable Synthesis of (Z)-9-Tricosene, the Housefly Sex Pheromone

Title:Practical and Scalable Synthesis of (Z)-9-Tricosene, the Housefly Sex Pheromone

Volume: 9 Issue: 9

Author(s): Miri Kim, Arigala Pitchaiah, No-Joong Park, In Taek Hwang and Kee-In Lee

Affiliation:

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

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.

Cite this article as:

Kim Miri, Pitchaiah Arigala, Park No-Joong, Hwang In Taek and Lee Kee-In, Practical and Scalable Synthesis of (Z)-9-Tricosene, the Housefly Sex Pheromone, Letters in Organic Chemistry 2012; 9 (9) . https://dx.doi.org/10.2174/157017812803521199