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

Publication Date:
31 December 2000 (online)

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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

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