ISSN:
0170-2041
Keywords:
Alcohols, branched and chiral
;
Grignard coupling
;
Pheromones
;
Sulfone, alkylation of
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of four stereoisomers of the female-produced sex pheromone [(2R,6R,10R)-, (2S,6R,10R)-, (2S,6S,10S)-, and (2R,6S,10S)-1a] of the rice moth (Corcyra cephalonica) was achieved by starting from (R)-2a, (R)- or (S)-3a, and (R)- or (S)-4 and using alkylation of alkyl phenyl sulfones as the coupling reaction. Behavioral bioassay of each isomer revealed (2R,6R,10R)-1a to be eight times more active than a diastereomeric mixture of equal amounts of the eight possible stereoisomers, indicating that (2R,6R,10R)-1a is probably the natural pheromone or at least the major component of the female blend. Electrophysiological bioassay also confirmed the high activity of (2R,6R,10R)-1a.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199119910144
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