Synthesis of Indoloquinolines: An Intramolecular Cyclization Leading to Advanced Perophoramidine-Relevant Intermediates

The bioactive natural product perophoramidine has proved a challenging synthetic target. An alternative route to its indolo[2,3-b]quinolone core structure involving a N-chlorosuccinimde-mediated intramolecular cyclization 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.

Automated summary

The study investigates the synthetic route of the bioactive natural product perophoramidine and an alternative N-chlorosuccinimde-mediated reaction for its core structure. Unexpected rearrangement of the core structure was observed during attempts to synthesize the natural product, with X-ray crystallographic analysis providing important analytical confirmation for the assigned structures.