Synthesis of reverse glycosyl fluorides via organophotocatalytic decarboxylative fluorination of uronic acids

Abstract

An efficient protocol for organophotocatalytic synthesis of reverse glycosyl fluorides (RGFs) is established relying on 9-mesityl-10-methyl-acridinium (Mes-Acr⁺)-mediated oxidative decarboxylative fluorination of uronic acids. Both pentofuranoid and hexopyranoid uronic acids are viable substrates for this transformation and a range of functional groups are tolerant. The potential of this reaction is highlighted by convenient synthesis of RGF-type nucleosides, in particular, those with a unique L-lyxo-configuration, thus providing a novel method to expand the chemical space of nucleosides which are widely applied in drug discovery and development.