Download PDF
Synthesis 2000; 2000(14): 2004-2008
DOI: 10.1055/s-2000-8716
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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