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Total Synthesis of Vancomycin Aglycon—Part 3: Final Stages
Author(s) -
Nicolaou K. C.,
Takayanagi Masaru,
Jain Nareshkumar F.,
Natarajan Swaminathan,
Koumbis Alexandros E.,
Bando Toshikazu,
Ramanjulu Joshi M.
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19981016)37:19<2717::aid-anie2717>3.0.co;2-i
Subject(s) - vancomycin , triazene , chemistry , cleavage (geology) , stereochemistry , combinatorial chemistry , glycopeptide , antibiotics , organic chemistry , biology , biochemistry , bacteria , staphylococcus aureus , paleontology , fracture (geology) , genetics
A triazene‐based synthetic strategy for the construction of the complex biaryl ethers and a Suzuki coupling reaction were the key steps in the synthesis of precursor 1 of the aglycon of vancomycin, which already contains the complete skeleton of the target compound. The cleavage of the triazene unit from the D ring and the removal of the other protecting groups led to the aglycon of vancomycin. These strategies should be particularly valuable for the synthesis of other naturally occurring glycopeptide antibiotics and offer opportunities for the synthesis of combinatorial libraries of compounds of the vancomycin family for chemical biology studies.