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Synthesis 2003(14): 2155-2160
DOI: 10.1055/s-2003-41051
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthetic Studies on d-Biotin, Part 6: [1] An Expeditious and Enantiocontrolled Approach to the Total Synthesis of d-Biotin via a Polymer-Supported Chiral Oxazaborolidine-Catalyzed Reduction of meso-Cyclic Imide Strategy

Fen-Er Chen*, Jian-Li Yuan, Hui-Fang Dai, Yun-Yan Kuang, Yong Chu
Department of Chemistry, Fudan University, Shanghai, 200433, P. R. China
Fax: +86(21)65642021; e-Mail: rfchen@fudan.edu.cn;
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Publication History

Received 19 May 2003
Publication Date:
22 August 2003 (online)

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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 C5 side chain at C4 in the thiolactone 9 via a Ni/C-catalyzed Fukuyama coupling reaction.

Key words

d-biotin - vitamin H - oxazaborolidine - polymer-supported chiral sulfonamide - enantioselective reduction - Fukuyama coupling reaction