Convenient synthesis of mosquito oviposition pheromone and a highly fluorinated analog retaining biological activity

Dawson, G., Mudd, A., Pickett, J. ORCID: https://orcid.org/0000-0002-8386-3770, Pile, M. and Wadhams, L. 1990. Convenient synthesis of mosquito oviposition pheromone and a highly fluorinated analog retaining biological activity. Journal of Chemical Ecology 16 (6) , pp. 1779-1789. 10.1007/BF01020494

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Abstract

A simple three-step synthesis is described for 6-acetoxy-5-hexadecanolide, the oviposition pheromone of the mosquitoCulex quinquefasciatus Say and others in that genus. An aldol condensation between 1-trimethylsilyloxycyclopent-1-ene and undecanal, followed by Baeyer-Villiger ring expansion and acetylation, gave the required compound as a 1∶1 mixture of diastereoisomers in high overall yield (>80%). This synthetic approach is readily adapted for synthesis of analogs. The heptadecafluoro compound, in which then-octyl group is replaced by perfluorooctyl, retained high biological activity.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Publisher:	Springer
ISSN:	0098-0331
Date of Acceptance:	12 February 1990
Last Modified:	10 Feb 2026 10:30
URI:	https://orca.cardiff.ac.uk/id/eprint/184497

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