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Determination of the Stereochemistry of the Aggregation Pheromone of Harlequin Bug, Murgantia histrionica

Ashot Khrimian, Shyam Shirali, Karl E. Vermillion, Maxime A. Siegler, Filadelfo Guzman, Kamlesh Chauhan, Jeffrey R. Aldrich, Donald C. Weber
Journal of chemical ecology 2014 v.40 no.11-12 pp. 1260-1268
Halyomorpha halys, Murgantia histrionica, X-ray diffraction, aggregation pheromones, enantiomers, males, nuclear magnetic resonance spectroscopy, stereochemistry
Preparation of a complete stereoisomeric library of 1,10-bisaboladien-3-ols and selected 10,11-epoxy-1-bisabolen-3-ols was pivotal for the identification of the aggregation pheromone of the brown marmorated stink bug, Halyomorpha halys. Herein, we describe syntheses of the remaining 10,11-epoxy-1-bisabolen-3-ols, and provide additional evidence on the assignment of relative and absolute configurations of these compounds by single-crystal X-ray crystallography of an intermediate, (3S,6R,7R,10S)-1-bisabolen-3,10,11-triol. To demonstrate the utility of this stereoisomeric library, we revisited the aggregation pheromone of the harlequin bug, Murgantia histrionica, and showed that the male-produced pheromone consists of two stereoisomers of 10,11-epoxy-1-bisabolen-3-ol. Employment of eight cis-10,11-epoxy-1-bisabolen-3-ol stereoisomeric standards, two enantioselective GC columns, and NMR spectroscopy enabled the identification of these compounds as (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol and (3S,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, which are produced by M. histrionica males in 1.4:1 ratio.