Determination of the relative and absolute configurations of the female-produced sex pheromone of the cerambycid beetle Prionus californicus

Joshua Rodstein, Jocelyn G Millar, James D Barbour, J Steven McElfresh, Ian M Wright, Karen S Barbour, Ann M Ray, Lawrence M Hanks
Journal of Chemical Ecology 2011, 37 (1): 114-24
We previously identified the basic structure of the female-produced sex attractant pheromone of the cerambycid beetle, Prionus californicus Motschulsky (Cerambycidae: Prioninae), as 3,5-dimethyldodecanoic acid. A synthesized mixture of the four stereoisomers of 3,5-dimethyldodecanoic acid was highly attractive to male beetles. Here, we describe stereoselective syntheses of three of the four possible stereoisomers, and the results of laboratory and field bioassays showing that male beetles are attracted specifically to (3R,5S)-3,5-dimethyldodecanoic acid, but not to its enantiomer, (3S,5R)-3,5-dimethyldodecanoic acid, indicating that the (3R,5S)-enantiomer is the active pheromone component. The diastereomeric (3R,5R)- and (3S,5S)-enantiomers were excluded from consideration because their gas chromatographic retention times were different from that of the insect-produced compound. The mixture of the four stereoisomers of 3,5-dimethyldodecanoic acid was as attractive to male P. californicus as the (3R,5S)-enantiomer, indicating that none of the other three stereoisomers inhibited responses to the active enantiomer. Beetles responded to as little as 10 ng and 10 μg of synthetic 3,5-dimethyldodecanoic acid in laboratory and field studies, respectively. Field studies indicated that capture rate did not increase with dosages of 3,5-dimethyldodecanoic acid greater than 100 μg. In field bioassays, males of a congeneric species, P. lecontei Lameere, were captured in southern California but not in Idaho.

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