Mild Approach to Nucleoside Analogues via Photoredox/Cu-Catalyzed Decarboxylative C–N Bond Formation. Total Synthesis of Oxetanocin A
Ruonan Wang, Hao Xu, Arpan Banerjee, Zhongwen Cui, Yuyong Ma, William G. Whittingham, Peng Yang, Ang Li
Abstract
The conventional N -glycosylation methods for nucleoside synthesis usually require strongly acidic or basic conditions. Here we report the decarboxylative C(sp 3 )–N coupling of glycosyl N -hydroxyphthalimide esters with nucleobases via dual photoredox/Cu catalysis, which offered a mild approach to nucleoside analogues. A total synthesis of oxetanocin A, an antiviral natural product containing an oxetanose moiety, has been achieved by using this method.
Topics & Concepts
ChemistryNucleosideNucleobaseGlycosylationGlycosylMoietyCatalysisTotal synthesisCombinatorial chemistryNatural productPhotoredox catalysisStereochemistryOrganic chemistryDNABiochemistryPhotocatalysisCatalytic C–H Functionalization MethodsCarbohydrate Chemistry and SynthesisSynthesis and Catalytic Reactions