Convenient synthesis of mosquito oviposition pheromone and a highly fluorinated analog retaining biological activity
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- Dawson, G.W., Mudd, A., Pickett, J.A. et al. J Chem Ecol (1990) 16: 1779. doi:10.1007/BF01020494
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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.