Vancomycin
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).
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).