SYNTHESIS OF ALL OF THE FOUR POSSIBLE STEREOISOMERS OF 4,8-DIMETHYLDECANAL, THE AGGREGATION PHEROMONE OF THE FLOUR BEETLES

Article abstract of DOI:10.1016/S0040-4020(01)91971-4

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.