Journal of Chemical Ecology (1999) 25, 1151-1162

Guan Qin Pu, M. Yamamoto, Y. Takeuchi, H. Yamazawa and T. Ando (1999)
Resolution of epoxydienes by reversed-phase chiral HPLC and its application to stereochemistry assignment of mulberry looper sex pheromone
Journal of Chemical Ecology 25 (5), 1151-1162
Abstract: Resolution of insect pheromonal cis-epoxydiene racemates derived from (Z,Z,Z)-3,6,9-trienes was examined with a reversed-phase chiral HPLC column. The results showed that a Chiralcel OJ-R column was suitable for separating the enantiomers having a C₁₇-C₂₃ unsaturated straight chain except for 9,10-epoxydienes with a C₂₁-C₂₃ chain. To determine the absolute configuration of the separated enantiomers, each of the optically active epoxydienes was hydrogenated over Pd-BaSO₄ and its behavior was examined on this chiral column by cochromatography with the corresponding chiral epoxy compound having a saturated chain, which was prepared via a Sharpless epoxidation reaction. This analysis showed that the dextrorotatory C₁₇-C₂₃ 3,4- and 6,7-epoxydienes and C₁₇-C₂₀ 9,10-epoxydienes with shorter R _ts possess (3S,4R)-, (6S,7R)-, and (9R,10S) configurations, respectively, and the levorotatory enantiomers with longer R _ts possess the opposite configuration. An abdominal tip extract of the mulberry looper, Hemerophila artilineata Butler (Lepidoptera: Geometridae: Ennominae), included (9S,10R)-(Z,Z)-cis-9,10-epoxy-3,6-octadecadiene as a main sex pheromone component. The synthetic (9S,10R)-9,10-epoxydiene, rather than its antipode, elicited strong antennal and behavioral responses from the male moths in electrophysiological and field tests.
(The abstract is excluded from the Creative Commons licence and has been copied with permission by the publisher.)
Link to article at publishers website
Database assignments for author(s): Tetsu Ando

Research topic(s) for pests/diseases/weeds:
pheromones/attractants/traps

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Pest and/or beneficial records:

Beneficial	Pest/Disease/Weed	Crop/Product	Country	Quarant.
	Phthonandria atrilineata