Synthesis of β-Hydroxy-β-(fluoronitrophenyl)alanines:  Vital Components in the Assembly of Biologically Active Cyclic Peptides

Craig A. Hutton
School of Chemistry, The University of Sydney, NSW 2006, Australia
Org. Lett., 1999, 1 (2), pp 295–298
DOI: 10.1021/ol9906054
Publication Date (Web): May 27, 1999
Copyright © 1999 American Chemical Society

Abstract

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Numerous biologically active cyclic peptides, such as the antibiotic vancomycin, contain amino acid residues connected through side-chain biaryl or aryl−alkyl ether linkages. Nucleophilic aromatic substitution reactions have recently been shown to provide a general method for the formation of such ether linkages, and consequently the synthesis of functionalized fluoronitro-substituted aromatic amino acids is of great interest. Herein, a method for the stereospecific synthesis of 3-fluoro-4-nitro- and 4-fluoro-3-nitro-threo-β-hydroxyphenylalanine is described.

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  • Published In Issue July 29, 1999
  • Received April 20, 1999

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