Journal of Chemical Ecology

, Volume 16, Issue 6, pp 1779–1789

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

  • Glenn W. Dawson
  • Alan Mudd
  • John A. Pickett
  • Mary M. Pile
  • Lester J. Wadhams
Article

DOI: 10.1007/BF01020494

Cite this article as:
Dawson, G.W., Mudd, A., Pickett, J.A. et al. J Chem Ecol (1990) 16: 1779. doi:10.1007/BF01020494

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.

Key words

Mosquito Culex quinquefasciatus Diptera Culicidae oviposition attractant pheromone synthesis acetoxyhexadecanolide perfluoroalkyl pheromone analog 

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • Glenn W. Dawson
    • 1
  • Alan Mudd
    • 1
  • John A. Pickett
    • 1
  • Mary M. Pile
    • 2
  • Lester J. Wadhams
    • 1
  1. 1.AFRC Institute of Arable Crops ResearchRothamsted Experimental StationHarpendenUK
  2. 2.London School of Hygiene & Tropical MedicineLondonUK

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