title: A modular approach to the total synthesis of tunicamycins.
abstract: 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.
authors: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China).
authors: Jiakun
authors: J
authors: Li
authors: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China). byu@mail.sioc.ac.cn.
authors: Biao
authors: B
authors: Yu
mesh_terms: D000215:Acylation; D000447:Aldehydes; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D006031:Glycosylation; D006046:Gold / Q000737:chemistry; D013237:Stereoisomerism; D014415:Tunicamycin / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000900:Anti-Bacterial Agents; D014415:Tunicamycin; D006046:Gold; C116609:3-hydroxybutanal
keywords: glycosylation; gold; nucleosides; total synthesis; tunicamycin