4.4 Article

A Rapid and Highly Diastereoselective Synthesis of Enantiomerically Pure (4R,5R)- and (4S,5S)-Isocytoxazone

Journal

SYNLETT
Volume -, Issue 10, Pages 1399-1402

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1260561

Keywords

diastereoselective; cytoxazone; tyrosine; oxazolidinone; oxidation

Funding

  1. Loughborough University
  2. Research Councils UK

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A three-step protocol for the highly diastereoselective (> 98%) synthesis of both (4R,5R)- and (4S,5S)-isocytoxazone from D-or L-tyrosine is reported. The diastereoselection was confirmed by X-ray crystallography. This synthesis is currently the highest yielding approach towards these enantiomerically pure biologically active oxazolidinones.

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