%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