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Indoline-fused polycycles were synthesized through a TFA-promoted intramolecular dearomative cyclization of indole-tethered pyrroles. Mechanistically, the strategic carbon-carbon bond formation is hypothesized to proceed via a Pictet-Spengler-type reaction wherein a reversal of conventional indole reactivity of tryptamine derivatives occurs. The synthetic versatility of this operationally simple, atom-economic approach is demonstrated in the preparation of the pyrido[1,2-a:3,4-b ‘]diindole core of natural product homofascaplysin C.
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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles