List   Previous   Next  

Publication 15  

  1. Total Synthesis of Vancomycin—Part 4: Attachment of the Sugar Moieties and Completion of the Synthesis
    K. C. Nicolaou, H. J. Mitchell, N. F. Jain, T. Bando, R. Hughes, N. Winssinger, S. Natarajan, A. E. Koumbis
    Chem. Eur. J. 1999, 5, 2648-2667

A number of valuable new synthetic strategies, such as the triazene-driven biaryl ether synthesis, have been developed during the total synthesis of vancomycin (1). Modern catalytic asymmetric reactions were employed for the construction of the required amino acid building blocks, which were then assembled to the appropriate peptide fragments, whose cyclization in the order C-O-D→AB/C-O-D→AB/C-O-D-E led to framework of the vancomycin aglycon (2). Sequential attachment of the required sugar moieties onto a suitably protected aglycon derivative, followed by deprotection, allowed the stereoselective total synthesis of the glycopeptide antibiotic vancomycin (1).

DOI: 10.1002/(SICI)1521-3765(19990903)5:9<2648::AID-CHEM2648>3.0.CO;2-Q 

open archive unige:24515