Washington State University

Rajendra P Singh

Donald S Matteson

Serricornin, the attractant pheromone of the cigarette beetle, is synthesized in high enantiomeric and diastereomeric purity via a series of reactions of asymmetric 2-(1-haloalkyl)-1,3,2-dioxaborolanes with Grignard reagents, which lead to the key intermediate �,S-(R*,R*,R*)!-2-ethyl-3,5-dimethyl-l-octen-6-ol. Oxidative cleavage of the carbon-carbon double bond of �S-(R*,R*,R*)!-2-ethyl-3,5-dimethyl-l-octen -6-ol with osmium tetroxide and sodium periodate yields serricornin.

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Moscow, ID, United States of America

Rajendra P Singh