Synthesis of 3′-deoxyadenosine-3′-spirocyclopropane, 3′-deoxy-uridine-3′-spirocyclopropane, and 5′-deoxy-4′,5′-methanoadenosine

Article abstract of DOI:10.1016/S0040-4039(00)73206-0

Cycloaddition of diazomethane with 3′-deoxy-3′-methylene- and 4′,5′-didehydro-5′-deoxynucleoside derivatives followed by sensitized photochemical extrusion of nitrogen provided the previously unreported 3′- and 4′-spirocyclopropane nucleoside derivatives. Enhancement of the cycloaddition reactions by electron withdrawing benzoyl protecting groups was observed.