Synthesis

Synthetic studies on d-biotin, part 6: an expeditious and enantiocontrolled approach to the total synthesis of d-biotin via a polymer-supported chiral oxazaborolidine- …

FE Chen, JL Yuan, HF Dai, YY Kuang, Y Chu

Index: Chen, Fen-Er; Yuan, Jian-Li; Dai, Hui-Fang; Kuang, Yun-Yan; Chu, Yong Synthesis, 2003 , # 14 p. 2155 - 2160

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Citation Number: 18

Abstract

Abstract An efficient and highly enantioselective synthesis of d-biotin from the known cis-1, 3- dibenzyl-2-imidazolidone-4, 5-dicarboxylic acid (5) was accomplished in 48% overall yield. The key reactions in the sequence involve the catalytic enantioselective reduction of meso- cyclic imide 6 using polymer-supported chiral oxazoborolidine, derived from (S)-α, α- diphenylprolinol and polymer-bound sulfonyl chloride, and the installation of the C 5 side ...