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Short Paper | Regular issue | Vol 92, No. 3, 2016, pp.544-551
Published online, 28th January, 2016
DOI: 10.3987/COM-15-13379
Preparation of (+)-Biotin: Process Development and Scale-up

Fei Xiong,* Jin Li, Gen Li, Bo Song, Yu-Xiao Zhou, Fen-Er Chen, and Dan Li

*Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China


A practical asymmetric total synthesis of (+)-biotin based upon the chiral bifunctional sulfamide 8-promoted enantioselective anhydride desymmetrization has been achieved via the key chiral intermediacy of (3aS,6aR)-1,3-bis(4-methoxybenzyl)tetrahydro-4H-thieno[3,4-d]imidazole-2,4(1H)-dione (4). In addition, the installation of the 4-carboxybutyl side chain at C-4 position of 4 was efficiently introduced by an improved C4+C1 strategy.