Atropisomerism, biphenyls and the Suzuki coupling: peptide antibiotics

The formidable synthetic challenge posed by the vancomycin class of glycope ptide antibiotics has only recently been met. Foremost among the difficulti es associated with the synthesis of these molecules is the control of non-c onventional stereochemical issues. These are a consequence of the molecules possessing biphenyl and biaryl ether linkages between amino acid residues situated within the constituent macrocycles. Among the keys to success is t he availability of methods that allow the efficient formation of biaryl lin kages between amino acid derivatives under mild conditions. Recent progress in the chemistry of the Suzuki coupling suggests that this constitutes a v ery powerful and general method for the synthesis of peptide biphenyls.