10.1021/acs.joc.7b02346.s001
Xin Zhou
Xin
Zhou
Peng Wang
Peng
Wang
Li Zhang
Li
Zhang
Pengwei Chen
Pengwei
Chen
Mingxu Ma
Mingxu
Ma
Ni Song
Ni
Song
Sumei Ren
Sumei
Ren
Ming Li
Ming
Li
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
American Chemical Society
2017
C-glycosylated phenanthridines
synthesis
pentapyranos -5-yl radicals
K 2 S 2 O 8
2017-12-20 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/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/5747187
We
have developed an efficient protocol for the synthesis of C-glycosylated
phenanthridines. Tetrafuranos-4-yl and pentapyranos-5-yl radicals,
generated from K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-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.