Vancomycin is a glycopeptide antibiotic, first introduced in the mid-1950s, with several important applications. These include the treatment of infections caused by different strains of MRSA (methicillin-resistant Staphylococcus aureus), also known as 'superbugs,' which can be highly problematic and even life-threatening. The complex structure of vancomycin incorporates three different types of chirality, with eighteen stereogenic centres, a biaryl axis, and two chloroaromatic rings whose restricted rotations introduce an element of planar chirality (a topic not covered here).

The structure of vancomycin
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For further information on vancomycin, see Chemistry, biology, and medicine of the glycopeptide antibiotics; K. C. Nicolaou, C. N. C. Boddy, S. Bräse and N. Winssinger, Angew. Chem. Int. Ed., 1999, 38, 2096–2152 (DOI: 10.1002/(SICI)1521-3773(19990802)38:15<2096::AID-ANIE2096>3.0.CO;2-F).

For a total synthesis, see Next-generation total synthesis of vancomycin; M. J. Moore, S. Qu, C. Tan, Y. Cai, Y. Mogi, D. J. Keith and D. L. Boger, J. Am. Chem. Soc., 2020, 142, 16039–16050 (DOI: 10.1021/jacs.0c07433).