%0 Generic %A Zhou, Xin %A Wang, Peng %A Zhang, Li %A Chen, Pengwei %A Ma, Mingxu %A Song, Ni %A Ren, Sumei %A Li, Ming %D 2017 %T Transition-Metal-Free Synthesis of C‑Glycosylated Phenanthridines via K2S2O8‑Mediated Oxidative Radical Decarboxylation of Uronic Acids %U https://acs.figshare.com/articles/dataset/Transition-Metal-Free_Synthesis_of_C_Glycosylated_Phenanthridines_via_K_sub_2_sub_S_sub_2_sub_O_sub_8_sub_Mediated_Oxidative_Radical_Decarboxylation_of_Uronic_Acids/5747184 %R 10.1021/acs.joc.7b02346.s002 %2 https://acs.figshare.com/ndownloader/files/10120128 %K C-glycosylated phenanthridines %K synthesis %K pentapyranos -5-yl radicals %K K 2 S 2 O 8 %X We have developed an efficient protocol for the synthesis of C-glycosylated phenanthridines. Tetrafuranos-4-yl and pentapyranos-5-yl radicals, generated from K2S2O8-mediated oxidative decarboxylation of furan- and pyranuronic acids, undergo attack to 2-isocyanodiphenyls and ensuing homolytic aromatic substitution to provide diverse C-glycosylated phenanthridines in satisfactory yields without resort to transition metals. This reaction tolerates various functional groups, and enables ready synthesis of complex oligosaccharide-based phenanthridines. The C-glycosylated phenanthridine derived from β-cyclodextrin has been prepared, which might be potential in medicinal and biological chemistry due to its flexible conformation. %I ACS Publications