50 光学活性昆虫フェロモンの合成研究

概要

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All of the possible stereoisomers of two aliphatic chiral pheromones were synthesized in optically pure states to establish the absolute stereochemistries of the natural products as well as to know the stereochemistry-biological activity relationship. 3,11-Dimethyl-2-nonacosanone (1) is the female sex pheromone of the German cockroach, Blattella germanica. Four stereoisomers of 1 were synthesized from (R)-(+)-citronellol employing the Grignard coupling reaction (A+B→C) as the key-step. The absolute configuration of the natural pheromone was shown to be 3S, 11S. All of the four isomers exhibited the same range of biological activity. erythro-3,7-Dimethyl-2-pentadecyl acetate or propionate (2) are the female sex pheromones of pine sawflies, Neodiprion lecontei, N. sertifer and Diprion similis. Four possible stereoisomers of 2 were synthesized from (R)-(+)-citronellol and (+)- or (-)-tartaric acids. The key-step was the S_N2 attack of a chiral organocopper reagent (E) to a chiral epoxide (D) to give a chiral alcohol (2a). This reaction provided pure erythro alcohols.
天然有機化合物討論会の論文
1978-08-22