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. 1982 Jul;25(7):881-4.
doi: 10.1021/jm00349a025.

Ring contraction of oleandrose on the macrolide antibiotic oleandomycin with [(Methoxycarbonyl)sulfamoyl]triethylammonium hydroxide inner salt

A A Nagel, J DiBrino, L A Vincent, J A Retsema

Ring contraction of oleandrose on the macrolide antibiotic oleandomycin with [(Methoxycarbonyl)sulfamoyl]triethylammonium hydroxide inner salt

A A Nagel et al. J Med Chem. 1982 Jul.

Abstract

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).

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