A Modular Approach to the Total Synthesis of Tunicamycins
| Autor: | Jiakun Li, Biao Yu |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
Aldehydes
Glycosylation Stereochemistry business.industry Acylation Tunicamycin Acetal Total synthesis Stereoisomerism General Chemistry General Medicine Modular design Catalysis Anti-Bacterial Agents carbohydrates (lipids) chemistry.chemical_compound chemistry Aldol reaction Intramolecular force Stereoselectivity Gold business Nucleoside |
| Zdroj: | Angewandte Chemie. 127:6718-6721 |
| ISSN: | 0044-8249 |
| Popis: | The tunicamycins constitute a delicate mimic of the bisubstrate intermediates of N-acetyl-D-hexosamine-1-phosphate translocases and thus inhibit bacterial cell-wall synthesis and the N glycosylation of eukaryotic proteins. An efficient approach to the synthesis of this unique type of nucleoside antibiotics is now reported and features the assembly of five modules in a highly stereoselective and robust manner. A Mukaiyama aldol reaction, intramolecular acetal formation, gold(I)-catalyzed O and N glycosylation, and final N acylation were used as the key steps. |
| Databáze: | OpenAIRE |
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