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Chemistry

Title:		"Total Synthesis, Stereochemical Assignment, and Field-Testing of the Sex Pheromone of the Strepsipteran Xenos peckii"
Author(s):		Zhai H; Hrabar M; Gries R; Gries G; Britton R;
Address:		"Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada. Department of Biological Sciences, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada. Department of Biological Sciences, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada. gries@sfu.ca. Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada. rbritton@sfu.ca"
Journal Title:		Chemistry
Year:		2016
Volume:		20160322
Issue:		18
Page Number:		6190 - 6193
DOI:		10.1002/chem.201505097
ISSN/ISBN:		1521-3765 (Electronic) 0947-6539 (Linking)
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"
Keywords:		Aldehydes/*chemistry Animals Gas Chromatography-Mass Spectrometry Insecta/*chemistry Magnetic Resonance Spectroscopy Male Pheromones/*chemical synthesis/chemistry Sex Attractants/*chemical synthesis/chemistry Stereoisomerism Suzuki-Miyaura Xenos peckii in;
Notes:		"MedlineZhai, Huimin Hrabar, Michael Gries, Regine Gries, Gerhard Britton, Robert eng Research Support, Non-U.S. Gov't Germany 2016/03/24 Chemistry. 2016 Apr 25; 22(18):6190-3. doi: 10.1002/chem.201505097. Epub 2016 Mar 22"