A four-step synthesis of erythro-m-chloro-3-hydroxytyrosine ethyl ester enantiomerically pure

Article abstract of DOI:10.1016/S0040-4039(98)00172-5

Pure erythro-m-chloro-3-hydroxytyrosine having the (2R,3R) configuration, a residue of Vancomycin and Aridicin A, has been prepared in 4 steps using an aldol addition involving a directly generated titanium enolate derived from a chiral iminoglycinate. (+)-Hydroxypinanone was used as a recoverable chiral auxiliary. The (2S,3S)-erythro isomer will be, of course, available from (-)-hydroxypinanone.