250273-58-6Relevant articles and documents
Total synthesis of vancomycin - Part 4: Attachment of the sugar moieties and completion of the synthesis
Nicolaou,Mitchell, Helen J.,Jain, Nareshkumar F.,Bando, Toshikazu,Hughes, Robert,Winssinger, Nicolas,Natarajan, Swaminathan,Koumbis, Alexandros E.
, p. 2648 - 2667 (2007/10/03)
The total synthesis of vancomycin (1, Figure 1) is described. The successful plan for this synthesis involves sequential and stereoselective coupling of vancomycin aglycon acceptor 6 and glycosyl donors, trichloroacetimidate 50 and glycosyl fluoride 27 (Scheme 8). Acceptor 6 was synthesized from vancomycin aglycon (2) (Scheme 1), which was derived both by total synthesis and by semisynthesis from vancomycin itself (1) (Scheme 2). The vancosamine derivative 27 was obtained by total synthesis (Scheme 3) while the glycosyl derivative 50 was prepared from glucal (46) (Scheme 6). A number of glycosidation model studies, carried out in order to establish the final route to vancomycin (1), are also described and so are a number of failed attempts to secure the target molecule (1).
