Synthesis of L-kedarosamine in protected form and its efficient incorporation into an advanced intermediate to kedarcidin chromophore

Abstract

An efficient route to the complex L-kedarosamine alpha-glycosidic ether 2, a synthetic precursor to kedarcidin chromophore, is described. Central to the route, which is suitable for the preparation of multigram amounts of material, is a short synthetic sequence from D-threonine to protected L-kedarosamine derivatives and methodology for their alpha-selective coupling with appropriate hydroxyl acceptors.