Abstract
From optically active (3Z,9Z)-cis-6,7-epoxy-3,9-henicosadiene (2), all stereoisomers 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 the cis-3,4-cis-6,7-diepoxy analog (3). Specifically, MCPBA oxidation of each enantiomer of this epoxydiene yielded a mixture of four compounds, namely two diastereomeric sets of leucomalure and the positional isomer, which were easily separable by chiral HPLC equipped with either a Chiralpak AD column 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 diepoxides.
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