| 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" |
| 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" |
