A modular approach to the total synthesis of tunicamycins.
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.
['Li|Jiakun|J|', 'Yu|Biao|B|']
D000215:Acylation D000447:Aldehydes D000900:Anti-Bacterial Agents D002384:Catalysis D006031:Glycosylation D006046:Gold D013237:Stereoisomerism D014415:Tunicamycin
total synthesis tunicamycin glycosylation nucleosides gold