Zhang, A., & Nie, J.Y. 2005 Enantioselective synthesis of the female sex pheromone of the pink hibiscus mealybug, Maconellicoccus hirsutus.. Journal of Agricultural and Food Chemistry 53(7): 2451-2455.
Notes: The pink hibiscus mealybug, Maconellicoccus hirsutus (Green), is an exotic insect pest and recently invaded Southern California and Florida. The female M. hirsutus releases the 2-methylbutanoate of a novel cyclobutanoid monoterpene alcohol (maconelliol) that together with lavandulyl 2-methylbutanoate constitutes the sex pheromone to attract males from a distance. Enantioselective syntheses of four different stereoisomers of the major component, maconelliyl 2-methylbutanoate 1, from alpha-pinene are reported. Absolute configurations of both naturally occurring maconelliyl 2-methylbutanoate 1 and the minor component, lavandulyl 2-methylbutanoate 2, have been established. Comparison of the analytical data of naturally occurring compounds with those of optically active synthetic isomers proved that both esters show the (R)-configuration at the alcohol and the (S)-configuration at acid moieties.