ISSN:
1573-1561
Keywords:
Mosquito
;
Culex quinquefasciatus
;
Diptera
;
Culicidae
;
oviposition
;
attractant
;
pheromone
;
synthesis
;
acetoxyhexadecanolide
;
perfluoroalkyl
;
pheromone analog
Source:
Springer Online Journal Archives 1860-2000
Topics:
Biology
,
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01020494
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