Expeditious Syntheses of Two Arylglycine Derivatives Corresponding to the Central Amino Acid of the Vancomycin Family of Antibiotics

Anthony J. Pearson; Mariappan V. Chelliah; Gilles C. Bignan

doi:10.1055/s-1997-1234

Synthesis 1997; 1997(5): 536-540
DOI: 10.1055/s-1997-1234

paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Expeditious Syntheses of Two Arylglycine Derivatives Corresponding to the Central Amino Acid of the Vancomycin Family of Antibiotics

Anthony J. Pearson^* , Mariappan V. Chelliah, Gilles C. Bignan

^*Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA, Fax +1(216)3683006; E-mail ajp4@po.cwru.edu

Abstract

PDF Download All articles of this category

Two expeditious and efficient syntheses (in 7 and 4 steps, respectively) are described for the central amino acid part of the vancomycin family. The first method constitutes a concise asymmetric synthesis, starting from 4-hydroxyphenylacetic acid, of (R)-(3,5-dihydroxy-4-methoxyphenyl)glycine derivatives using Evans’ asymmetric azidation methodology. In the second approach, an efficient synthesis of a protected 3,5-dichloro-4-methoxyphenylglycine derivative is described, starting from commercially available (R)-4-hydroxyphenylglycine. These two syntheses are much shorter and operationally simpler than those previously described, and are currently employed in an effort towards the construction of the bicyclic system of vancomycin and ristocetin.

vancomycin - antibiotic - arylglycine - asymmetric synthesis - amino acid

PDF (521 kb)