PHEROMONE SYNTHESIS .119. A NEW SYNTHESIS OF THE 4 STEREOISOMERS OF 3,11-DIMETHYL-2-NONACOSANONE, THE FEMALE-PRODUCED SEX-PHEROMONE OF THE GERMAN-COCKROACH

被引:25
作者
MORI, K
TAKIKAWA, H
机构
[1] Department of Agricultural Chemistry, The University of Tokyo, Bunkyo-ku, Tokyo, 113
关键词
D O I
10.1016/S0040-4020(01)85576-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The pure four stereoisomers of 3,ll-dimethyl-2-nonacosanone (1), the female-produced sex pheromone of the German cockroach, were synthesized starting from (R)-citronellol (2a) and ethyl (R)-3-hydroxybutanoate (3). The key step was the chromatographic separation of (5RS,6R)-6-hydroxy-5-methyl-2-heptanone (16a) to give pure (5R,6R- and) 5S,6R-isomers. All of the four stereoisomers of 1 were bioactive. © 1990.
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页码:4473 / 4486
页数:14
相关论文
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  • [11] Nishida R., 1983, Memoirs of the College of Agriculture, Kyoto University, P1