Amino acid based diastereoselective synthesis of elsaminose

Article abstract of DOI:10.1016/0040-4039(96)01173-2

Optically pure (+)-elsaminose (2), the amino sugar contained in the antitumor antibiotic elasmicin A, has been synthesized in eight steps (26% overall yield) from known building blocks derived from glycine, L-valine, and L-threonine. Direct and selective construction of the key intermediate 6, with the complete backbone and the proper stereochemical configuration, is accomplished by a syn-aldol type reaction between lithiated Schollkopf's bislactime ether 5 and a 1,3-dioxolane-4-carboxaldehyde (-)-3.