A Convenient Preparation of Optically Active Diepoxyhenicosene (Leucomalure), Lymantrid Sex Pheromone, by Chiral HPLC

✍ Scribed by Masanobu Yamamoto; Hiroyuki Yamazawa; Naoto Nakajima; Tetsu Ando

• Book ID: 101280092
• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 224 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199907)1999:7<1503::aid-ejoc1503>3.0.co;2-6

✦ Synopsis

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

(3R,4S,6S,7R) isomers of (9Z)-cis-3,4-cis-6,7-diepoxy-9- [a] Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, MCPBA oxidation of (6R,7S)-2 produced another mix-