Synthetic Studies on d-Biotin, Part 9. An Improved Asymmetric Synthetic Route to d-Biotin via Hoffmann–Roche Lactone–Thiolactone Approach

Fen-Er Chen; Hui-Qing Jia; Xu-Xiang Chen; Hui-Fang Dai; Bin Xie; Yun-Yan Kuang; Jian-Feng Zhao

doi:10.1248/cpb.53.743

Regular Articles

Synthetic Studies on d-Biotin, Part 9. An Improved Asymmetric Synthetic Route to d-Biotin via Hoffmann–Roche Lactone–Thiolactone Approach

Fen-Er Chen, Hui-Qing Jia, Xu-Xiang Chen, Hui-Fang Dai, Bin Xie, Yun-Yan Kuang, Jian-Feng Zhao

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Keywords: d-biotin, vitamin H, polymer-supported oxazaborolidine, asymmetric reduction, Wittig reaction, desymmetrization

JOURNAL FREE ACCESS

2005 Volume 53 Issue 7 Pages 743-746

DOI https://doi.org/10.1248/cpb.53.743

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Abstract

An efficient and highly stereoselective total synthesis of d-biotin has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid (2) with an overall yield of 33%. Polymer-supported oxazaborolidine-catalyzed asymmetric reduction of meso-cyclic imide 4 constitutes the key synthetic step in introducing stereogenic centers into the d-biotin molecule.

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