Synthetic Studies on (+)-Biotin, Part 15: A Chiral Squaramide-Mediated Enantioselective Alcoholysis Approach toward the Total Synthesis of (+)-Biotin

Xu-Xiang Chen; Fei Xiong; Han Fu; Zhi-Qian Liu; Fen-Er Chen

doi:10.1248/cpb.59.488

Notes

Synthetic Studies on (+)-Biotin, Part 15: A Chiral Squaramide-Mediated Enantioselective Alcoholysis Approach toward the Total Synthesis of (+)-Biotin

Xu-Xiang Chen, Fei Xiong, Han Fu, Zhi-Qian Liu, Fen-Er Chen

著者情報

キーワード: (+)-biotin, cinchona alkaloid-derived squaramide, enantioselective alcoholysis, tricyclic thiophanium salt

ジャーナルフリー

2011 年 59 巻 4 号 p. 488-491

DOI https://doi.org/10.1248/cpb.59.488

詳細

抄録

An efficient stereocontrolled total synthesis of (+)-biotin (1) has been achieved via the intermediacy of Roche's lactone 5 starting from cis-1,3-dibenzyl-2-imidazole-4,5-dicarboxylic acid (2). The bifunctional cinchona alkaloid-derived squaramide-promoted enantioselective alcoholysis was utilizing as a tool for the construction of two contiguous stereocenters of C-3a and C-6a in biotin molecular with excellent enantioselectivity. In addition, the 4-carboxybutyl side chain was assembled by first using C4+C1 approach via a novel tricyclic thiophanium salt intermediate.

責任著者(Corresponding author)

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