title: Enantioselective synthesis of the female sex pheromone of the pink hibiscus Mealybug, Maconellicoccus hirsutus.
abstract: 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.
authors.affiliation: Chemicals Affecting Insect Behavior Laboratory, Agricultural Research Service, U.S. Department of Agriculture, Beltsville Agriculture Research Center-West, Beltsville, Maryland 20705, USA. zhanga@ba.ars.usda.gov
authors.forename: Aijun
authors.initials: A
authors.lastname: Zhang
authors.forename: Junying
authors.initials: J
authors.lastname: Nie
mesh_terms: D000818:Animals; D000081008:Bicyclic Monoterpenes; D002087:Butyrates / Q000138:chemical synthesis / Q000737:chemistry; D003128:Coma; D003503:Cyclobutanes / Q000138:chemical synthesis / Q000737:chemistry; D005260:Female; D006430:Hemiptera; D008968:Molecular Conformation; D039821:Monoterpenes / Q000737:chemistry; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C488425:(2,2-dimethyl-3-(1-methylethylidene)cyclobutyl)methyl 2-methylbutanoate; D000081008:Bicyclic Monoterpenes; D002087:Butyrates; D003503:Cyclobutanes; D039821:Monoterpenes; D012724:Sex Attractants; C005451:alpha-pinene