Ring contraction of oleandrose on the macrolide antibiotic oleandomycin with [(Methoxycarbonyl)sulfamoyl]triethylammonium hydroxide inner salt.
Ring contraction of the neutral oleandrose sugar in the 14-membered-ring macrolide antibiotic oleandomycin (2) has been accomplished using [(methoxycarbonyl)sulfamoyl]triethylammonium hydroxide inner salt (1). The product of this interesting rearrangement, after methanolic hydrolysis of the 2'-acetate, is the 11-acetyl-3-O-(3"-methoxy-4"-vinylfuranosyl)oleandomycin (12). The in vitro activity of furanoside 12 is only moderately less than that of 11-acetyloleandomycin (13).
D001419:Bacteria / Q000187:drug effects; D001426:Bacterial Proteins / Q000096:biosynthesis; D055598:Chemical Phenomena; D002621:Chemistry; D003837:Deoxy Sugars; D006601:Hexoses; D009827:Oleandomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000644:Quaternary Ammonium Compounds
D001426:Bacterial Proteins; D003837:Deoxy Sugars; D006601:Hexoses; D000644:Quaternary Ammonium Compounds; C035441:oleandrose; C035442:((methoxycarbonyl)sulfamoyl)triethylammonium; D009827:Oleandomycin