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Total Synthesis of Vancomycin—Part 1: Design and Development of Methodology
Author(s) -
Nicolaou K. C.,
Li Hui,
Boddy Christopher N. C.,
Ramanjulu Joshi M.,
Yue TaiYuen,
Natarajan Swaminathan,
Chu XinJie,
Bräse Stefan,
Rübsam Frank
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19990903)5:9<2584::aid-chem2584>3.0.co;2-b
Subject(s) - glycopeptide , vancomycin , glycopeptide antibiotic , combinatorial chemistry , chemistry , stereoselectivity , derivative (finance) , total synthesis , stereochemistry , antibiotics , catalysis , organic chemistry , biochemistry , biology , bacteria , genetics , staphylococcus aureus , financial economics , economics
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 ).