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

Author:
Ashot Khrimian, Shyam Shirali, Karl E. Vermillion, Maxime A. Siegler, Filadelfo Guzman, Kamlesh Chauhan, Jeffrey R. Aldrich, Donald C. Weber
Source:
Journal of chemical ecology 2014 v.40 no.11-12 pp. 1260-1268
ISSN:
0098-0331
Subject:
Halyomorpha halys, Murgantia histrionica, X-ray diffraction, aggregation pheromones, enantiomers, males, nuclear magnetic resonance spectroscopy, stereochemistry
Abstract:
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.
Agid:
60199
Handle:
10113/60199