Synthetic Studies on (+)-Biotin, Part 15: A Chiral Squaramide-Mediated Enantioselective Alcoholysis Approach toward the Total Synthesis of (+)-Biotin
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概要
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An efficient stereocontrolled total synthesis of (+)-biotin (1) has been achieved via the intermediacy of Roches 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.
著者
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Chen Xu-xiang
Fudan-dsm Joint Lab. For Synthetic Method And Chiral Technol. Dep. Of Chemistry Fudan Univ.
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Xiong Fei
Fudan-DSM Joint Laboratory for Synthetic Method and Chiral Technology, Department of Chemistry, Fuda
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Fu Han
Fudan-DSM Joint Laboratory for Synthetic Method and Chiral Technology, Department of Chemistry, Fuda
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Liu Zhi-Qian
Fudan-DSM Joint Laboratory for Synthetic Method and Chiral Technology, Department of Chemistry, Fuda
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Chen Fen-Er
Fudan-DSM Joint Laboratory for Synthetic Method and Chiral Technology, Department of Chemistry, Fuda
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Liu Zhi-Qian
Fudan-DSM Joint Laboratory for Synthetic Method and Chiral Technology, Department of Chemistry, Fudan University
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Fu Han
Fudan-DSM Joint Laboratory for Synthetic Method and Chiral Technology, Department of Chemistry, Fudan University
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Chen Xu-Xiang
Fudan-DSM Joint Laboratory for Synthetic Method and Chiral Technology, Department of Chemistry, Fudan University
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Chen Fen-Er
Fudan-DSM Joint Laboratory for Synthetic Method and Chiral Technology, Department of Chemistry, Fudan University
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Xiong Fei
Fudan-DSM Joint Laboratory for Synthetic Method and Chiral Technology, Department of Chemistry, Fudan University
関連論文
- Synthetic Studies on (+)-Biotin, Part 15: A Chiral Squaramide-Mediated Enantioselective Alcoholysis Approach toward the Total Synthesis of (+)-Biotin
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