Synthetic Studies on (+)-Biotin, Part 15: A Chiral Squaramide-Mediated Enantioselective Alcoholysis Approach toward the Total Synthesis of (+)-Biotin
| Autor: | Fen-Er Chen, Han Fu, Zhi-Qian Liu, Fei Xiong, Xu-Xiang Chen |
|---|---|
| Rok vydání: | 2011 |
| Předmět: |
chemistry.chemical_classification
biology Chemistry Stereochemistry Enantioselective synthesis Squaramide Biotin Cinchona Total synthesis Stereoisomerism General Chemistry General Medicine biology.organism_classification Amides Stereocenter chemistry.chemical_compound Drug Discovery Dicarboxylic Acids Bifunctional Lactone |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 59:488-491 |
| ISSN: | 1347-5223 0009-2363 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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