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Construction of Indole Structure on Pyrroloindolines via AgNTf2‑Mediated Amination/Cyclization Cascade: Application to Total Synthesis of (+)-Pestalazine B
journal contribution
posted on 2019-05-20, 14:37 authored by Hiroyuki Hakamata, Hirofumi Ueda, Hidetoshi TokuyamaAn N-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-endo-dig cyclization.
In this reaction, AgNTf2 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.
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dimeric indole alkaloidbromo groupApplicationMediatedConstructionπ- Lewis acidPestalazinesynthesisAgNTf 23 a-positiontandem reagentSwitchingAminationcascade processα- carbolinepestalazineindole structureσ- Lewis acidpyrroloindoline derivativesPyrroloindoline2- ethynylanilinesCascadefuroindolinesilver-mediated aminationTotal Synthesisbromopyrroloindolinealkyne moietyIndole Structure5- endo-dig cyclization
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