A synthesis of bredinin (Mizoribine®) from an acyclic precursor

Abstract Bredinin (4-carbamoyl-1-β- d -ribofuranosylimidazolium-5-olate, 1 ) was synthesised by the formation of a malonamate from 2,3-isopropylidene- d -ribofuranosylamine and ethyl malonyl chloride, followed by a sequence involving amination, via reduction of an oxime, heterocycle formation and then deprotection.