75 リパーゼの不斉認識能を利用する光学活性天然有機化合物の合成(ポスター発表の部)

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Lipases are useful in enantioselective hydrolysis and synthesis of esters. In this paper, syntheses of some optically active natural products utilizing the ability of lipases to distinguish the chiralities of synthetic substrates are described. 1. Synthesis of Frontalin 1: Synthesis of 1 can be replaces by the synthesis of dihydroxyketone 2, which was derived from S-3, obtained via Lipase OF catalyzed hydrolysis (Scheme 1). 2. Synthesis of Mevalonolactone 11: The recovered ester R-3 in the above hydrolysis is a tailor-made starting material for mevalonolactone 11. One carbon homologation utilizing the benzyl protecting group to the carboxylic terminal accomplised the synthesis of mevalonolactone 11 (Scheme 2). 3. Synthesis of Brevicomin 17, 18: endo- and exo-Brevicomin (17, 18) can be prepared from common intermediate R-19. We expected that such "optically active protected hydroxy ketone intermediate" can be obtained via enantio-selective hydrolysis of enol ester dl-20. In fact, Lipase OF again worked well as shown in Scheme 3. 4. Enzyme-Mediated Lactonization in Organic Solvents: Even in an anhydrous organic medium, some lipases can keep their activities, and in such case they catalyze transesterification instead of hydrolysis. Intramolecular reactions of this type can be utilized in the synthesis of optically active lactones. Insect pheromones, hexadecanolide R-23 and γ-lactone 26 are synthesized from racemic hydroxy esters 22 and 24, respectively, by the action of Lipase P and PPL (Scheme 4).
天然有機化合物討論会の論文
1990-09-25

75 リパーゼの不斉認識能を利用する光学活性天然有機化合物の合成(ポスター発表の部)

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