A convenient preparation of optically active diepoxyhenicosene (leucomalure), lymantrid sex pheromone, by chiral HPLC

From optically active (3Z,9Z)-cis-6,7-epoxy-3,9-henicosadiene (2), all ster eoisomers of (3Z)-cis-6,7-cis-9,10-diepoxy-3-henicosene [leucomalure (1)], a sex pheromone component of the Satin moth, were prepared in addition to t he cis-3,4-cis-6,7-diepoxy analog (3). Specifically, MCPBA oxidation of eac h enantiomer of this epoxydiene yielded a mixture of four compounds, namely two diastereomeric sets of leucomalure and the positional isomer, which we re easily separable by chiral HPLC equipped with either a Chiralpak AD colu mn or a Chiralcel OJ-R column. Their chemical structures were determined by 2D-NMR analyses, and it was further confirmed that the chiral HPLC columns also had a high capability of resolving the enantiomers of these diepoxide s.