MIMICS OF L-RHAMNOSE - SYNTHESIS OF C-GLYCOSIDES OF L-RHAMNOFURANOSE AND AN ALPHA-AZIDOESTER AS DIVERGENT INTERMEDIATES FOR COMBINATORIAL GENERATION OF RHAMNOFURANOSE LIBRARIES

The ring contraction of readily available delta-lactones provides a sh ort route to the synthesis of both epimers of C-L-rhamnofuranosides, r adical bromination of which give access to an alpha-azidocarboxylate a s a divergent intermediate for applying combinatorial methodology for the preparation of a wide range of mimics of L-rhamnofuranose; such ma terials may provide an approach to the study of the biosynthesis of th e cells walls of mycobacteria such as Mycobacterium tuberculosis and M . leprae.