15 固定化パン酵母の生物変換機能を利用する数種のフェロモン類の不斉合成(ポスター発表の部)

概要

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Asymmetric synthesis of some lactonic pheromones has been investigated through combination of enzymatic and chemical procedures. Our strategy for biotransformation of organic substrates is the use of immobilized biocatalysts in aqueous solutions and in water-organic solvent two-phase systems. For the synthesis of two enantiomers of phoracantholide I (1), diethyl 3-oxoglutarate was regioselectively alkylated and subsequently hydrolyzed with decarboxylation to give a keto acid. The keto acid was then subjected to an enzymatic reduction with immobilized baker's yeast entrapped in gels of carrageenan to produce the corresponding chiral hydroxy acid. The chiral hydroxy acid was converted to both (R)- and (S)-1 by known chemical procedures. The utility of the present methodology of combined enzymatic and chemical system is also demonstrated by the preparation of each enantiomer of 5-hexadecanolide (2) and 4-dodecanolide (3). As a result of the reuse of the baker's yeast immobilized in carrageenan beads, it has become clear that immobilized baker's yeast shows outstanding reproducibility for optical purities of the product.
天然有機化合物討論会の論文
1988-09-26