Stereoselective Synthesis of 4,5-Dihydroxy-D-erythro- and 4,5-Dihydroxy-D-threo-L-norvaline from D-Ribonolactone

  • Ariza J
  • Díaz M
  • Font J
 et al. 
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Abstract

Nitrogen functions have been introduced stereoselectively at the C-2 position in D-ribonolactone derivatives in order to prepare the title unnatural amino acids. The synthetic strategies lie in the inversion of configuration in SN2-type substitution reactions and stereospecific hydrogenation of conveniently substituted butenolides. The threo-isomer is the key precursor in the synthesis of the antibiotic clavalanine. © 1993.

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Authors

  • Jesús Ariza

  • Miguel Díaz

  • Josep Font

  • Rosa M. Ortuño

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