Expedient synthesis of threo-beta-hydroxy-alpha-amino acid derivatives: phenylalanine, tyrosine, histidine, and tryptophan.

ABSTRACT: An expedient synthesis of enantiomerically pure threo-beta-hydroxy-alpha-amino acid derivatives of phenylalanine, tyrosine, histidine, and tryptophan is described. The NBS-mediated radical bromination of the N,N-di-tert-butoxycarbonyl protected alpha-amino acids and subsequent treatment with silver nitrate in acetone provided the trans-oxazolidinones predominantly. Cesium carbonate catalyzed hydrolysis then generated the beta-hydroxy amino acid derivatives in excellent overall yield.

SUBMITTER: Crich D 

PROVIDER: S-EPMC2621330 | biostudies-literature | 2006 Sep

REPOSITORIES: biostudies-literature