34 リパーゼ不斉変換反応を基盤とする光学活性天然物の合成(ポスター発表の部)
詳細
In recent years, we have systematically investigated the possibility of using bakers' yeast and lipases as a practical reagent in organic synthesis. As a continuing effort toward the chemoenzymatic synthesis of optically active natural products, we here present the synthesis of chiral pheromones through enzyme-catalyzed transformation using lipase P (Pseudomonas fluorescens lipase). (2R,6S,10S)-Trimethyl-2-pentadecanol [(2R,6S,10S)-15], one of the stereoisomers of the sex pheromone of Corcyra cephalonica Stainton, was synthesized in highly optically pure form by the two-step hydrolysis of the 2,2,2-trichloroethyl carbonate derivative (2RS,6S,10S)-15a with lipase P. The same resolution method led to stereochemically pure (2R,8R)-8-methyl-2-decanol propionate [(2R,8R)-24], which is a component of the sex pheromone of Diabrotica species. (3R,6E)-7-Methyl-6-nonen-3-ol acetate [(R)-quadrilure, (R)-32], the aggregation pheromone of Cathartus quadricollis, was synthesized in enantiomerically and geometrically pure form by the enzyme-catalyzed hydrolysis of racemic 32 with lipase P, followed by enzyme-catalyzed transesterification with PPL. A similar procedure for the preparation of (S)-32 will also be described.
