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

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.