Nonconventional Stereochemical Issues in the Design of the Synthesis of the Vancomycin Antibiotics: Challenges Imposed by Axial and Nonplanar Chiral Elements in the Heptapeptide Aglycons

Controlling the elements of planar and axial chirality are the principal challenges in the synthesis of the aglycon of vancomycin. Vancomycin is the prototypical member of the glycopeptide family of antibiotics which are effective for the treatment of infections by methicillin‐resistant Staphylococc...

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Veröffentlicht in:	Angewandte Chemie International Edition 1998-10, Vol.37 (19), p.2704-2708
Hauptverfasser:	Evans, David A., Dinsmore, Christopher J., Watson, Paul S., Wood, Michael R., Richardson, Timothy I., Trotter, B. Wesley, Katz, Jeffrey L.
Format:	Artikel
Sprache:	eng
Schlagworte:	Antibiotics Atropisomerism Chirality Nucleophilic aromatic substitutions Vancomycin
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creator	Evans, David A. Dinsmore, Christopher J. Watson, Paul S. Wood, Michael R. Richardson, Timothy I. Trotter, B. Wesley Katz, Jeffrey L.
description	Controlling the elements of planar and axial chirality are the principal challenges in the synthesis of the aglycon of vancomycin. Vancomycin is the prototypical member of the glycopeptide family of antibiotics which are effective for the treatment of infections by methicillin‐resistant Staphylococcus aureus. The first total syntheses of the vancomycin and eremomycin aglycons provide insight into the influence of structure on kinetic and thermodynamic control of atropselective macrocyclizations.
doi_str_mv	10.1002/(SICI)1521-3773(19981016)37:19<2704::AID-ANIE2704>3.0.CO;2-1
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source	Wiley Online Library Journals Frontfile Complete
subjects	Antibiotics Atropisomerism Chirality Nucleophilic aromatic substitutions Vancomycin
title	Nonconventional Stereochemical Issues in the Design of the Synthesis of the Vancomycin Antibiotics: Challenges Imposed by Axial and Nonplanar Chiral Elements in the Heptapeptide Aglycons
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