39 酵素化学的手法を用いたプロスタグランジンの合成

概要

論文の詳細を見る
As a part of our synthetic studies on biologically active compounds consisting of five membered ring, we have succeeded in the synthesis of prostaglandins and the related compounds, such as carbacyclin and 11-deoxy PGE_1 by means of enzymic procedure. 1. Synthesis of carbacyclin using microbial reduction. The kinetical resolution of (±)-1 was screened by means of the microbial reduction using forty species of yeast. Among these, Kloeckera saturnus and Pichia farinosa afforded the optically active (-)-1 in 17% (96%ee) and 27% (93%ee) yields, respectively. The chemical conversion of (-)-1 into the key intermediate (9) for carbacyclin was achieved by ring-contraction with Tl(NO_3)_3. 2. Synthesis of 11-deoxy PGE_1 using enzymic hydrolysis. Enzymic hydrolysis of the meso-diacetate (16) was studied. Among the tested enzymes, Rhizopus delemar lipase afforded the optically active monoacetate ((-)-20) in 84% yield (>99%ee). The monoacetate ((-)-20) was effectively converted into the synthetic intermediate (33) for 11-deoxy PGE_1.
天然有機化合物討論会の論文
1986-09-09