title: Convenient synthesis of mosquito oviposition pheromone and a highly fluorinated analog retaining biological activity.
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.
authors.affiliation: AFRC Institute of Arable Crops Research, Rothamsted Experimental Station, AL5 2JQ, Harpenden, Hertfordshire, UK.
authors.forename: G W
authors.initials: GW
authors.lastname: Dawson
authors.forename: A
authors.initials: A
authors.lastname: Mudd
authors.forename: J A
authors.initials: JA
authors.lastname: Pickett
authors.forename: M M
authors.initials: MM
authors.lastname: Pile
authors.forename: L J
authors.initials: LJ
authors.lastname: Wadhams