An efficient and enantioselective synthesis of d-biotin

Authors
Chen, FE Huang, YD Fu, H Cheng, Y Zhang, DM Li, YY Peng, ZZ
Citation
Fe. Chen et al., An efficient and enantioselective synthesis of d-biotin, SYNTHESIS-S, (14), 2000, pp. 2004-2008
Citations number
38
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
14
Year of publication
2000
Pages
2004 - 2008
Database
ISI
SICI code
0039-7881(200012):14<2004:AEAESO>2.0.ZU;2-2
Abstract
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 thioa nhydride 8 to prepare the (3aS, 6aR)- thiolactone 9 and the introduction of the C-6 side chain at C-2 in 9 via a modified Grignard reaction. This nove l synthesis proceeded in six steps to afford 1 with 21% overall yield.