8 生化学的方法によるキラル合成原料の調製(口頭発表の部)

概要

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Preparation of chiral building blocks by biochemical methods including asymmetric reduction with baker's yeast, utilization of biopolymer and asymmetric hydrolysis with lipase is described. The following topics are discussed. 1) Both the enantiomers of ethyl 3-hydroxybutanoate [1a] were prepared and utilized as the chiral starting material for the synthesis of pityol [2]. 2) A hydroxy ester [4] was prepared by baker's yeast reduction of oxoester [5] and utilized as the chiral starting material for the synthesis of sporogen AO-1 [6]. 3) Asymmetric reductions of symmetrical diketones [9,14] by yeasts were carried out, and the products [8,13] were converted to JH III [12], JH I [20], and JH II [21]. 4) Bridged symmetrical diketones [23,26] were reduced by baker's yeast to give hydroxy ketones [22,24]. The latter is a chiral starting material for the synthesis of glycinoeclepin A [25]. 5) A monoacetate (+)-[27a], useful starting material for the synthesis of optically active prostaglandins, was prepared using hydrolysis of readily obtainable substrate by commecially available lipases.
天然有機化合物討論会の論文
1987-07-25