100566-56-1Relevant articles and documents
Practical and scalable synthesis of (Z)-9-Tricosene, the housefly sex pheromone
Kim, Miri,Pitchaiah, Arigala,Park, No-Joong,Hwang, In Taek,Lee, Kee-In
, p. 628 - 631 (2012)
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.