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
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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.
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(5):5201-5208.
Zhang, Tao; Ma, Wei-Li; Li, Tian-Rui; Wu, Jia; Wang, Jun-Run; Du, Zhen-Ting. 2013. "A Facile Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth." Molecules 18, no. 5: 5201-5208.