« Previous AbstractConstruction and analysis of cDNA libraries from the antennae of male and female cotton bollworms Helicoverpa armigera (Hubner) and expression analysis of putative odorant-binding protein genes    Next Abstract"Male- and Female-Biased Gene Expression of Olfactory-Related Genes in the Antennae of Asian Corn Borer, Ostrinia furnacalis (Guenee) (Lepidoptera: Crambidae)" »

Molecules

Title:		"A facile asymmetric synthesis of (s)-14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth"
Author(s):		Zhang T; Ma WL; Li TR; Wu J; Wang JR; Du ZT;
Address:		"College of Sciences, Northwest A&F University Yangling 712100, Shaanxi, China"
Journal Title:		Molecules
Year:		2013
Volume:		20130507
Issue:		5
Page Number:		5201 - 5208
DOI:		10.3390/molecules18055201
ISSN/ISBN:		1420-3049 (Electronic) 1420-3049 (Linking)
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 Li(2)CuCl(4)-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 Li(2)CuCl(4)-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:		Animals Moths/*chemistry Sex Attractants/*chemical synthesis/*chemistry;
Notes:		"MedlineZhang, Tao Ma, Wei-Li Li, Tian-Rui Wu, Jia Wang, Jun-Run Du, Zhen-Ting eng Research Support, Non-U.S. Gov't Switzerland 2013/05/09 Molecules. 2013 May 7; 18(5):5201-8. doi: 10.3390/molecules18055201"