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

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

1,†
,
1,†
,
1
,
1
,
1
 and
1,2,*
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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Abstract

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 (CC BY 3.0).

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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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