Convenient synthesis of mosquito oviposition pheromone and a highly fluorinated analog retaining biological activity
- 1 June 1990
- journal article
- research article
- Published by Springer Nature in Journal of Chemical Ecology
- Vol. 16 (6) , 1779-1789
- https://doi.org/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.Keywords
This publication has 16 references indexed in Scilit:
- Attractancy and species specificity of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromoneJournal of Chemical Ecology, 1987
- A short, stereodivergent synthesis of the racemic erythro and threo diastereomers of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromoneTetrahedron Letters, 1986
- Asymmetric synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide, the major component of the oviposition attractant pheromone of the mosquito Culex pipiens fatigans, and two of its stereoisomersThe Journal of Organic Chemistry, 1986
- Some fluorine‐containing pheromone analoguesPesticide Science, 1986
- Stereoselective synthesis of the major component of a mosquito oviposition attractant pheromone from a β-lithiopropionate equivalentTetrahedron, 1986
- Studies on the identification and syntheses of insect pheromones XXI stereoselective synthesis of all the possible optical isomers of the mosquito oviposition attractant pheromoneTetrahedron Letters, 1985
- Absolute configuration of mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolideJournal of Chemical Ecology, 1985
- An oviposition attractant pheromone in Culex quinquefasciatus Say (Diptera: Culicidae)Bulletin of Entomological Research, 1985
- erythro-6-Acetoxy-5-hexadecanolide, the major component of a mosquito oviposition attractant pheromoneJournal of the Chemical Society, Chemical Communications, 1982
- The Influence of the Apical Droplet of Culex Egg Rafts on Oviposition of Culex Pipiens Faticans (Diptera: Culicidae)Journal of Medical Entomology, 1979