Synthesis of indoloquinolines: an intramolecular cyclization leading to advanced Perophoramidine-relevant intermediates

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Abstract

The bioactive natural product perophoramidine has proved a challenging synthetic target. An alternative route to its indolo[2,3-b]quinolone core structure involving an N-chlorosuccinimde mediated intramolecular cylization reaction is reported. Attempts to progress towards the natural product are also discussed with an unexpected deep-seated rearrangement of the core structure occurring during an attempted iodoetherification reaction. X-ray crystallographic analysis provides important analytical confirmation of assigned structures.
Original languageEnglish
Article number6039
Number of pages19
JournalMolecules
Volume26
Issue number19
DOIs
Publication statusPublished - 5 Oct 2021

Keywords

  • Intramolecular cyclization
  • X-ray structure
  • Perophoramidine
  • Natural product
  • Claisen rearrangement
  • Indoloquinoline

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