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Discovery of the Aggregation Pheromone of the Brown Marmorated Stink Bug (Halyomorpha halys) through the Creation of Stereoisomeric Libraries of 1-Bisabolen-3-ols

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U.S. Department of Agriculture, Agricultural Research Service, Beltsville Area, IIBBL, Maryland 20705, United States
The Institute of Cellular and Organismic Biology, Academia Sinica, Taipei, Taiwan 115
U.S. Department of Agriculture, Agricultural Research Service, NCAUR, Peoria, Illinois 61604, United States
Department of Chemistry, Johns Hopkins University, Baltimore, Maryland 21218, United States
U.S. Department of Agriculture, Agricultural Research Service, AFRL, Kearneysville, West Virginia 25430, United States
*Phone: 301-504-6138. E-mail: [email protected]
Cite this: J. Nat. Prod. 2014, 77, 7, 1708–1717
Publication Date (Web):June 25, 2014
https://doi.org/10.1021/np5003753
Copyright © 2014 The American Chemical Society and American Society of Pharmacognosy

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    Abstract

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    We describe a novel and straightforward route to all stereoisomers of 1,10-bisaboladien-3-ol and 10,11-epoxy-1-bisabolen-3-ol via the rhodium-catalyzed asymmetric addition of trimethylaluminum to diastereomeric mixtures of cyclohex-2-enones 1 and 2. The detailed stereoisomeric structures of many natural sesquiterpenes with the bisabolane skeleton were previously unknown because of the absence of stereoselective syntheses of individual stereoisomers. Several of the bisabolenols are pheromones of economically important pentatomid bug species. Single-crystal X-ray crystallography of underivatized triol 13 provided unequivocal proof of the relative and absolute configurations. Two of the epoxides, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (3) and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (4), were identified as the main components of a male-produced aggregation pheromone of the brown marmorated stink bug, Halyomorpha halys, using GC analyses on enantioselective columns. Both compounds attracted female, male, and nymphal H. halys in field trials. Moreover, mixtures of stereoisomers containing epoxides 3 and 4 were also attractive to H. halys, signifying that the presence of additional stereoisomers did not hinder attraction of H. halys and relatively inexpensive mixtures can be used in monitoring, as well as control strategies. H. halys is a polyphagous invasive species in the U.S. and Europe that causes severe injury to fruit, vegetables, and field crops and is also a serious nuisance pest.

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    Dehydration products from compounds 512 and selected gas chromatograms thereof, entire CIF file for triol 13, as well as Tables S1–S6 and 1H and 13C NMR spectra of all new compounds are available free of charge via the Internet at http://pubs.acs.org.

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