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Molecules 2013, 18(5), 5201-5208; doi:10.3390/molecules18055201

A Facile Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth

1 College of Sciences, Northwest A&F University Yangling 712100, Shaanxi, China 2 Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 20032, China These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 28 March 2013 / Revised: 27 April 2013 / Accepted: 28 April 2013 / Published: 7 May 2013
(This article belongs to the Section Organic Synthesis)
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An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth has been achieved. The target molecule was synthesized in six linear steps and in 30.3% overall yield from commercially available hexanoyl chloride, (S)-4-benzyloxazolidin-2-one and 1,9-nonanediol. The hexanoyl chloride was connected with (S)-4-benzyloxazolidin-2-one, and with the induction of the chiral oxazolidinone auxiliary, after chiral methylation, LAH reduction and then tosylation gave the chiral key intermediate 5 in high stereoselectivity. 1,9-Nonanediol, was selectively brominated, THP protected and subjected to Li2CuCl4-mediated C-C coupling to afford a C12 intermediate. The target molecule, (S)-14-methyl-1-octadecene, was obtained after the two parts were subjected to a second Li2CuCl4-mediated C-C coupling. Our synthetic approach represents the first time a substrate-control asymmetric synthesis of (S)-14-methyl-1-octadecene has been reported.
Keywords: 14-methyl-1-octadecene; asymmetric synthesis; peach leafminer moth; (S)-4-benzyloxazolidin-2-one 14-methyl-1-octadecene; asymmetric synthesis; peach leafminer moth; (S)-4-benzyloxazolidin-2-one
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


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Zhang, T.; Ma, W.-L.; Li, T.-R.; Wu, J.; Wang, J.-R.; Du, Z.-T. A Facile Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth. Molecules 2013, 18, 5201-5208.

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