ISSN:
1434-193X
Keywords:
Diepoxy sex pheromone
;
Chiral HPLC
;
Resolution
;
Stereochemistry
;
Diepoxyhenicosene
;
Leucomalure
;
Lymantrid satin moth
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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