Synthesis of the C-glycoside fragment of nogalamycin and some nogalamycin precursors

Abstract

A short, stereoselective method for generation of the fused C-glycoside unit of the anticancer agent nogalamycin is described; in particular, synthesis of the D,E,F ring system. The method utilises a total synthesis of the glycosidic unit from an aryl furyl alcohol. Initial studies are described for the preparation of highly substituted phthalides, useful for the further annulation of the D,E,F ring system to the rest of the nogalamycin skeleton.