Syntheses and Determination of Absolute Configurations and Biological Activities of the Enantiomers of the Longtailed Mealybug Pheromone

Preparation
and assignment of absolute configurations to both enantiomers
of the sex pheromone of the longtailed mealybug, an irregular monoterpenoid
with extraordinary biological activity, has been completed. Comparison
of the biological activities of both enantiomers and the racemate
in field trials showed that the (S)-(+)-enantiomer
was highly attractive to male mealybugs, strongly suggesting that
female longtailed mealybugs produce this enantiomer. The (R)-(−)-enantiomer was benign, being neither attractive
nor inhibitory.