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

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

Journal Name: Letters in Organic Chemistry

Volume 9 , Issue 9 , 2012

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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

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Article Details

VOLUME: 9
ISSUE: 9
Year: 2012
Page: [628 - 631]
Pages: 4
DOI: 10.2174/157017812803521199

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