SUGAR-MODIFIED URIDINE BISVINYL SULFONE - SYNTHESIS OF A BIFUNCTIONALIZED NUCLEOSIDE MICHAEL ACCEPTOR AND ITS USE IN STEREOSELECTIVE TANDEMCYCLIZATION

A bisvinyl sulfone functionality is incorporated into the carbohydrate moiety of uridine to synthesize 6 (or 7) which is a bifunctionalized nucleoside Michael acceptor and has the potential to form covalent bon d with biological nucleophiles. This compound could be used to generat e a large number and a new class of bicyclic S,S-dioxidethiazine deriv atives 8-12 in stereoselective fashion. Compound 6 is also useful for the synthesis of a wide variety of monosubstituted compounds 13-15. Th e structures of compounds 8-12 have been established unambiguously by synthesising the core structure 28 in a stereospecific fashion.