6 キラルなアレンなどの光学活性な脂肪族昆虫フェロモンの合成

概要

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Our recent syntheses of chiral insect pheromones have enabled us to recognize the importance of absolute stereochemistry in determining pheromone activity. In order to carry out accurate bioassays, we must synthesize optically pure pheromones in sufficient quantities. Herein we give three examples of such chiral syntheses. 1) (3S, 11S)-29-Hydroxy-3,11-dimethylnonacosan-2-one 1. This is the pheromone of the German cockroach, Blattella germanica. (R)-(+)-Citronellic acid was the starting material. 2) Methyl (R, E)-tetradeca-2,4,5-trienoate 27. This is the pheromone of the dried bean beetle, Acanthoscelides obtectus. The synthesis started from (R)-undec-1-yn-3-ol which was obtained by conventional resolution. 3) (S)-Sulcatol 35a. This is the pheromone of Gnathotrichus retusus. The crucial step was the yeast reduction of ethyl acetoacetate.
天然有機化合物討論会の論文
1980-09-10