Synthetic studies on (+)-biotin, part 15: A chiral squaramide-mediated enantioselective alcoholysis approach toward the total synthesis of (+)-biotin |
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Authors: | Chen Xu-Xiang Xiong Fei Fu Han Liu Zhi-Qian Chen Fen-Er |
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Institution: | Fudan-DSM Joint Laboratory for Synthetic Method and Chiral Technology, Department of Chemistry, Fudan University. |
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Abstract: | 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. |
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