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 s equence in which C-glycosylation of dehydrorabelomycin dimethyl ether serve d as the key step. The use of a S-azido 2,3,6-trideoxy pyranose as an activ ated equivalent of a 5-dimethyl-amino 2,3,6-trideoxy sugar was demonstrated in this reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.