64 フェノール類の不斉酸化カップリングによる天然物の合成

概要

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It has long been recognized that oxidative coupling of phenols serves as a key-step in the biosynthesis of many classes of natural products. However, none of the enzymatic oxidative coupling of phenols in vitro has given optically active products. In order to elucidate asymmetric biosynthetic process of lignans, we set out to try oxidative coupling of coniferyl alcohol (2) with horseradish peroxidase-hydrogen peroxide in the media using various carbohydrates to afford dehydrodiconiferyl alcohol (4) and pinoresinol (5), and obtained following results. 1) Under various concentration of monosaccharides or disaccharides in a phosphate buffer, optical yields of 4 and 5 are 0〜9.8% (e.e.). 2) Under saturated solution of dextrin or starch, optical yield of 4 increased to 18% or 15% respectively. 3) Under saturated solution of β-cyclodextrin, optical yield of 4 exhibited the maximum (100% e.e.) at pH 8.04. Other attempts to synthesize natural products under the same conditions using β-cyclodextrin are in progress.
天然有機化合物討論会の論文
1981-09-10