Relative Reactivities of Aminoglycosides and their Synthetic Equivalents in the C-Glycosylation of Aromatics. Synthesis of the Pseudoaglycone (d-C-Glycoside) of the Benzanthrins

The pseudoaglycone of the benzanthrin antibiotics was prepared by a short sequence in which C-glycosylation of dehydrorabelomycin dimethyl ether served as the key step. The use of a 3-azido 2,3,6-trideoxy pyranose as an activated equivalent of a 3-dimethylamino 2,3,6-trideoxy sugar was demonstrated in this reaction.