Stereoselective synthesis of chloramphenicol from D-serine

Article abstract of DOI:10.1016/S0040-4039(98)01848-6

An efficient synthesis of the widely used antibiotic chloramphenicol (1) is described. The key step in the synthesis involves chelation-controlled addition of phenylmagnesium bromide to a suitably protected D-serinal derivative, affording the pivotal D-threo 1,2-amino alcohol intermediate 3 in a highly stereoselective manner.