- A facile asymmetric synthesis of (S)-14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth
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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 Li 2CuCl4-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.
- Zhang, Tao,Ma, Wei-Li,Li, Tian-Rui,Wu, Jia,Wang, Jun-Run,Du, Zhen-Ting
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p. 5201 - 5208
(2013/06/27)
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- Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica
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Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5-9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,SR)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.
- Tai, Akira,Syouno, Emi,Tanaka, Kazuki,Fujita, Morifumi,Sugimura, Takashi,Higashiura, Yasutomo,Kakizaki, Masashi,Hara, Hideho,Naito, Tikahiko
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p. 111 - 121
(2007/10/03)
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- Pheromone synthesis, CXCII. - Synthesis of all the stereoisomers of 10,14-dimethyloctadec-1-ene, 5,9-dimethyloctadecane and 5,9- dimethylheptadecane, the sex pheromone components of the apple leafminer, Lyonetia prunifoliella
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All of the stereoisomers of 10,14-dimethyloctadec-1-ene (1), 5,9- dimethyloctadecane (2) and 5,9-dimethylheptadecane (3), the sex pheromone components of the apple leafminer (Lyonetia prunifoliella), were synthesized by starting from the enantiomers of ci
- Tamagawa, Hideki,Takikawa, Hirosato,Mori, Kenji
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p. 973 - 978
(2007/10/03)
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- Pheromone Synthesis, CXXIX - Synthesis of the (5S,9S)-Isomers of 5,9-Dimethylheptadecane and 5,9-Dimethyloctadecane, the Major and the Minor Components of the Sex Pheromone of Leucoptera malifoliella Costa
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The synthesis of (5S,9S)-5,9-dimethylheptadecane (1) as well as that of (5S,9S)-5,9-dimethyloctadecane (2) has been achieved by starting from methyl (R)-3-hydroxy-2-methylpropanoate (3a) and (S)-citronellal (7). --- Key Words: Heptadecane, 5,9-dimethyl- /
- Mori, Kenji,Wu, Jiang
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p. 439 - 444
(2007/10/02)
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