Total synthesis of aryl C-glycoside antibiotics

Abstract

An approach to the regio- and stereocontrolled synthesis of aryl C-glycoside antibiotics is described. The key reaction is the Lewis acid-mediated formation of aryl O-glycosides and its in situ conversion to C-glycosides (O→C-glycoside rearrangement). The utility of this reaction is demonstrated in the total syntheses of vineomycinone B2 (1) and gilvocarcin M (2) and V (3). The latter synthesis established the absolute stereochemistry of the gilvocarcins. © 1994 IUPAC