✦ LIBER ✦

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

✍ Scribed by David A. Evans; Christopher J. Dinsmore; Paul S. Watson; Michael R. Wood; Timothy I. Richardson; B. Wesley Trotter; Jeffrey L. Katz

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 185 KB
Volume: 37
Category: Article
ISSN: 0044-8249
DOI: 10.1002/(sici)1521-3773(19981016)37:19<2704::aid-anie2704>3.0.co;2-1

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✦ Synopsis

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.