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Synlett 1993; 1993(1): 51-53
DOI: 10.1055/s-1993-22345
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A New Approach to the Synthesis of γ-Keto-α-Amino Acids: Synthesis of Optically Pure 5-Hydroxy-4-oxo-L-norvaline, L-HON

Jack E. Baldwin* , Robert M. Adlington, Christopher R. A. Godfrey, David W. Gollins, Marie L. Smith, Andrew T. Russel
  • *The Dyson Perrins Laboratory and the Oxford Centre for Molecular Sciences, South Parks Rd., Oxford, OX1 3QY, England
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Publication History

Publication Date:
19 March 2002 (online)

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The nucleophilic ring opening of activated monocyclic (β-lactams by trimethylsulphoxonium ylide, lithiated sulphones and cuprates is reported. Conversion of the resultant ring opened forms to a variety of funtionalised γ-keto-α-amino acids is described as exemplified by a short synthesis of the natural product 5-hydroxy-4- oxo-L????-noivaline, L????-HON.