1. Total Synthesis of Vancomycin—Part 1: Design and Development of Methodology
- Author
-
Tai-Yuen Yue, Hui Li, Stefan Bräse, Swaminathan Natarajan, Christopher N. Boddy, Frank Rübsam, Xin-Jie Chu, Joshi M. Ramanjulu, and Kyriacos C. Nicolaou
- Subjects
chemistry.chemical_classification ,Stereochemistry ,medicine.drug_class ,Organic Chemistry ,Total synthesis ,Peptide ,General Chemistry ,Glycopeptide antibiotic ,Combinatorial chemistry ,Catalysis ,Amino acid ,Williamson ether synthesis ,chemistry.chemical_compound ,chemistry ,medicine ,Vancomycin ,Stereoselectivity ,Derivative (chemistry) ,medicine.drug - Abstract
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).
- Published
- 1999
- Full Text
- View/download PDF