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Synthesis of all of the four possible stereoisomers of 4,8-dimethyldecanal, the aggregation pheromone of the flour beetles

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
39
Issue
14
Identifiers
DOI: 10.1016/s0040-4020(01)91971-4

Abstract

Abstract The four stereoisomers of 4,8-dimethyldecanal were synthesized employing organometallic or electrolytic coupling reactions as the key-step. The response of the red flour beetle, Tribolium castaneum, to the ( 4R, 8R)-isomer was identical with that to the natural pheromone, while other isomers induced only very weak or no responses. The ( 4R, 8R)-isomer is therefore the natural pheromone.

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