An Efficient and Enantioselective Synthesis of d-Biotin

Fen-Er Chen; Yao-Dong Huang; Han Fu; Yu Cheng; Dao-Ming Zhang; Yong-Ye Li; Zuo-Zong Peng

doi:10.1055/s-2000-8716

Synthesis 2000; 2000(14): 2004-2008
DOI: 10.1055/s-2000-8716

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An Efficient and Enantioselective Synthesis of d-Biotin

Fen-Er Chen^* , Yao-Dong Huang, Han Fu, Yu Cheng, Dao-Ming Zhang, Yong-Ye Li, Zuo-Zong Peng

^*Department of Chemistry, Fudan University, Shanghai, 200433, People's Republic of China; Fax +86(21)65 64 17 40; E-mail: rfchen@fudan.edu.cn

Abstract

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An efficient and enantioselective synthesis of d-biotin 1 starting from cis 1,3-dibenzyl-2-imidazo-lidone-4,5-dicarboxylic acid (6) is described. The key steps are the enantioselective reduction of meso-1,2-dicarboxylic thioanhydride 8 to prepare the (3aS,6aR)-thiolactone 9 and the introduction of the C₆ side chain at C-2 in 9 via a modified Grignard reaction. This novel synthesis proceeded in six steps to afford 1 with 21% overall yield.

d-biotin - vitamin H - (R)-BINAL-H - enantioselective reduction - Grignard reaction

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