Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers
| Autor: | Shengyang Wang, Jian-Song Sun, Yachen Zhao, Biao Yu, Xin Cao, Gong-Li Tang, Qingju Zhang |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Glycosylation Stereochemistry 010405 organic chemistry Diastereomer Total synthesis General Chemistry General Medicine 010402 general chemistry 01 natural sciences Catalysis Amino acid 0104 chemical sciences chemistry.chemical_compound chemistry Aldol condensation Stereoselectivity Epimer Nucleoside |
| Zdroj: | Angewandte Chemie. 130:2934-2938 |
| ISSN: | 0044-8249 |
| Popis: | The proposed diastereoisomers (1 a-d) together with their C8'-epimers (1 e-h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio- and stereocontrolled gold(I)-catalyzed N-glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3' in amipurimycin should be of opposite configuration. |
| Databáze: | OpenAIRE |
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