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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 9, Issue 9, 2012

Page: [628 - 631] Pages: 4

DOI: 10.2174/157017812803521199

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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