| Title: | "Enantioselective synthesis of the female sex pheromone of the pink hibiscus Mealybug, Maconellicoccus hirsutus" |
| Address: | "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" |
| ISSN/ISBN: | 0021-8561 (Print) 0021-8561 (Linking) |
| 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" |
| Keywords: | Animals Bicyclic Monoterpenes Butyrates/chemical synthesis/chemistry Coma Cyclobutanes/chemical synthesis/chemistry Female *Hemiptera Molecular Conformation Monoterpenes/chemistry Sex Attractants/*chemical synthesis/chemistry Stereoisomerism; |
| Notes: | "MedlineZhang, Aijun Nie, Junying eng 2005/03/31 J Agric Food Chem. 2005 Apr 6; 53(7):2451-5. doi: 10.1021/jf048198k" |
