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

[ Vol. 9 , Issue. 9 ]

Author(s):

Miri Kim, Arigala Pitchaiah, No-Joong Park, In Taek Hwang and Kee-In Lee   Pages 628 - 631 ( 4 )

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

Affiliation:

Green Chemistry Division, Korea Research Institute of Chemical Technology, P.O. Box 107, Yuseong, Taejon 305-600, Korea.



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