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Construction of Indole Structure on Pyrroloindolines via AgNTf<sub>2</sub>‑Mediated Amination/Cyclization Cascade: Application to Total Synthesis of (+)-Pestalazine B

By Hiroyuki Hakamata (4446532), Hirofumi Ueda (1748680) and Hidetoshi Tokuyama (1748674)


An <i>N</i>-linked indole structure was constructed on the 3a-position of pyrroloindoline derivatives via a cascade process involving silver-mediated amination of bromopyrroloindolines with 2-ethynylanilines with subsequent 5-<i>endo-dig</i> cyclization. In this reaction, AgNTf<sub>2</sub> was used as a tandem reagent, which activated the bromo group as a σ-Lewis acid and the alkyne moiety as a π-Lewis acid. Switching from the initial step to the second step was conducted by controlling the temperature. This protocol was applied to the synthesis of various pyrroloindolines, α-carboline, and furoindolines and the total synthesis of a dimeric indole alkaloid, (+)-pestalazine B

Topics: Biophysics, Biochemistry, Medicine, Microbiology, Genetics, Molecular Biology, Neuroscience, Physiology, Biotechnology, Infectious Diseases, Plant Biology, Computational Biology, Chemical Sciences not elsewhere classified, dimeric indole alkaloid, bromo group, Application, Mediated, Construction, π- Lewis acid, Pestalazine, synthesis, AgNTf 2, 3 a-position, tandem reagent, Switching, Amination, cascade process, α- carboline, pestalazine, indole structure, σ- Lewis acid, pyrroloindoline derivatives, Pyrroloindoline, 2- ethynylanilines, Cascade, furoindoline, silver-mediated amination, Total Synthesis, bromopyrroloindoline, alkyne moiety, Indole Structure, 5- endo-dig cyclization
Year: 2019
DOI identifier: 10.1021/acs.orglett.9b01399.s001
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Provided by: FigShare
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