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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Hrabar, Michael Gries, Regine Gries, Gerhard Britton, Robert Zhai, Huimin |
| Description | Author Affiliation: Zhai H ( Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.); Hrabar M ( Department of Biological Sciences, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.); Gries R ( Department of Biological Sciences, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.); Gries G ( Department of Biological Sciences, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada. gries@sfu.ca.); Britton R ( Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada. rbritton@sfu.ca.) |
| Abstract | The sex pheromone of the endoparasitoid insect Xenos peckii (Strepsiptera: Xenidae) was recently identified as (7E,11E)-3,5,9,11-tetramethyl-7,11-tridecadienal. Herein we report the asymmetric synthesis of three candidate stereostructures for this pheromone using a synthetic strategy that relies on an $sp^{3}–sp^{2}$ Suzuki–Miyaura coupling to construct the correctly configured C7-alkene function. Comparison of $^{1}H NMR$ spectra derived from the candidate stereostructures to that of the natural sex pheromone indicated a relative configuration of (3R*,5S*,9R*). Chiral gas chromatographic (GC) analyses of these compounds supported an assignment of (3R,5S,9R) for the natural product. Furthermore, in a 16-replicate field experiment, traps baited with the synthetic (3R,5S,9R)-enantiomer alone or in combination with the (3S,5R,9S)-enantiomer captured 23 and 18 X. peckii males, respectively (mean±SE: 1.4±0.33 and 1.1±0.39), whereas traps baited with the synthetic (3S,5R,9S)-enantiomer or a solvent control yielded no captures of males. These strong field trapping data, in combination with spectroscopic and chiral GC data, unambiguously demonstrate that (3R,5S,9R,7E,11E)-3,5,9,11-tetramethyl-7,11-tridecadienal is the X. peckii sex pheromone. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 18 |
| Volume Number | 22 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2016-04-25 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Aldehydes Chemistry Insects Pheromones Chemical Synthesis Sex Attractants Animals Gas Chromatography-Mass Spectrometry Magnetic Resonance Spectroscopy Stereoisomerism Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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