Stereoselective synthesis of N-boc-galantinic acid ethyl ester

Article abstract of DOI:10.1016/S0040-4039(98)02614-8

An efficient synthesis of the biologically important title amino acid is described. The key features of the synthesis are, i) a chelation controlled Grignard reaction towards stereoselective formation of the syn-1,2-amino alcohol unit, and ii) construction of the anti-1,3-diol moiety via hydroxy group directed stereoselective reduction of a proximal ketone.