Among the glycopeptide family of antibiotics vancomycin is the most effective in combating bacterial infection. The structural complexity together with the numerous stereocenters has made it a challenging target for synthetic chemists. Emerging bacterial resistance against vancomycin has inspired scientists to look at its synthesis from the standpoint of developing new antibiotics.

One of the key feature of vancomycin structure, the biaryl ether linkage, can be synthesized in various ways. We are using a ruthenium mediated S_NAr reaction to selectively displace fluorine over chlorine to make the aryl ether linkage as well as to gain control over the atropisomer formation. Preliminary results have shown an absolute chemoselectivity as only fluorine was selectively displaced. Studies are underway to extend this result to our current synthetic strategy.