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Millar JG, Giblin M, Barton D, et al. Synthesis and field screening of chiral monounsaturated epoxides as lepidopteran sex attractants and sex pheromone components. J Chem Ecol. 1991;17(5):911-29doi: 10.1007/BF01395599.
Millar, J. G., Giblin, M., Barton, D., & Underhill, E. W. (1991). Synthesis and field screening of chiral monounsaturated epoxides as lepidopteran sex attractants and sex pheromone components. Journal of chemical ecology, 17(5), 911-29. https://doi.org/10.1007/BF01395599
Millar, J G, et al. "Synthesis and field screening of chiral monounsaturated epoxides as lepidopteran sex attractants and sex pheromone components." Journal of chemical ecology vol. 17,5 (1991): 911-29. doi: https://doi.org/10.1007/BF01395599
Millar JG, Giblin M, Barton D, Underhill EW. Synthesis and field screening of chiral monounsaturated epoxides as lepidopteran sex attractants and sex pheromone components. J Chem Ecol. 1991 May;17(5):911-29. doi: 10.1007/BF01395599. PMID: 24259075.
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J Chem Ecol. 1991 May;17(5):911-29. doi: 10.1007/BF01395599.

Synthesis and field screening of chiral monounsaturated epoxides as lepidopteran sex attractants and sex pheromone components.

Journal of chemical ecology

J G Millar, M Giblin, D Barton, E W Underhill

Affiliations

  1. Department of Entomology, University of California, 92521, Riverside, California.

PMID: 24259075 DOI: 10.1007/BF01395599

Abstract

Enantiomerically enriched forms of (Z)-6-cis-9,10-epoxymonoenes and (Z)-9-cis-6,7-epoxymonoenes of chain lengths C17-20 were synthesized by Sharpless asymmetric epoxidation of allylic alcohol intermediates, followed by tosylation or halogenation and chain extension. The resulting monounsaturated epoxides were field tested as sex attractants for lepidopteran species.Euchlaena madusaria Walker males were attracted to blends of the enantiomers of (Z)-6- cis- 9,10-epoxynonadecene 6Z-cis-9,10-epoxy-19:H; IUPAC name [2α,3α(Z)]-2-pentyl-3-(2-dodecenyI)oxirane in combination with 6Z,9Z-19: H. The response was antagonized by 9Z-cis-6,7-epoxy-19: H. 6Z,9Z-19: H was tentatively identified in pheromone gland extracts.Xanthotype sospeta Drury male moths were attracted to lures containing 6Z-9S,10R-epoxy-19: H; the response was antagonized by the opposite enantiomer.Pal-this angulalis Hübner males were attracted to 9Z-6S,7R-epoxy-19:H; the opposite enantiomer was antagonistic. 6Z,9Z-19:H and 9Z-cis-6,7-epoxy-19:H and 9Z-cis-6,7-epoxy-19:H were tentatively identified in pheromone gland extracts fromAnacamptodes humaria Guenée females. In field trails, 9Z-6R,7S-epoxy-19:H proved to be the attractive enantiomer, and the response was potentiated by 6Z,9Z-19:H. Mechanisms by which unique chemical communication channels are maintained by each species are discussed.

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