title: A facile asymmetric synthesis of (s)-14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth.
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.
authors: College of Sciences, Northwest A&F University Yangling 712100, Shaanxi, China.
authors: Tao
authors: T
authors: Zhang
authors: Wei-Li
authors: WL
authors: Ma
authors: Tian-Rui
authors: TR
authors: Li
authors: Jia
authors: J
authors: Wu
authors: Jun-Run
authors: JR
authors: Wang
authors: Zhen-Ting
authors: ZT
authors: Du
mesh_terms: D000818:Animals; D009036:Moths / Q000737:chemistry*; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D012724:Sex Attractants
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