ABSTRACT
Vancomycin was the first glycopeptide antibiotic to be isolated and is one member of a large family of antibiotics that are becoming increasingly important pharmaceutical agents in the treatment of severe staphlococcal infections. In 1978, a proposal for the structure of vancomycin was extended by Williams et al. The development of a laboratory mimic to duplicate nature’s approach to these bond constructions in vancomycin might arguably provide the pivotal methodology for a convergent laboratory synthesis of this family of natural products. The disaccharide appended to the phenol of residue can be hydrolyzed under mild conditions to provide vancomycin aglycone and the amino sugar vancosamine. The vancomycin structure arguably provides one of nature’s most elegant illustrations of atropisomerism. Vancomycin presents the unique problem of having the amino acid side chains oxidatively cross-linked to provide a tricyclic structure. An alternative strategy to macrolactamization could be based on vancomycin’s proposed biosynthesis.
