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Article

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

School of Chemistry and Biomedical Sciences Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews KY16 9ST, UK
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Academic Editors: Gianfranco Favi, William T. A. Harrison, R. Alan Aitken and Paul Waddell
Molecules 2021, 26(19), 6039; https://doi.org/10.3390/molecules26196039
Received: 14 September 2021 / Revised: 30 September 2021 / Accepted: 1 October 2021 / Published: 5 October 2021
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. View Full-Text
Keywords: perophoramidine; natural product; Claisen rearrangement; indoloquinoline; intramolecular cyclization; X-ray structure perophoramidine; natural product; Claisen rearrangement; indoloquinoline; intramolecular cyclization; X-ray structure
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MDPI and ACS Style

Johnston, C.A.; Cordes, D.B.; Lebl, T.; Slawin, A.M.Z.; Westwood, N.J. Synthesis of Indoloquinolines: An Intramolecular Cyclization Leading to Advanced Perophoramidine-Relevant Intermediates. Molecules 2021, 26, 6039. https://doi.org/10.3390/molecules26196039

AMA Style

Johnston CA, Cordes DB, Lebl T, Slawin AMZ, Westwood NJ. Synthesis of Indoloquinolines: An Intramolecular Cyclization Leading to Advanced Perophoramidine-Relevant Intermediates. Molecules. 2021; 26(19):6039. https://doi.org/10.3390/molecules26196039

Chicago/Turabian Style

Johnston, Craig A., David B. Cordes, Tomas Lebl, Alexandra M.Z. Slawin, and Nicholas J. Westwood 2021. "Synthesis of Indoloquinolines: An Intramolecular Cyclization Leading to Advanced Perophoramidine-Relevant Intermediates" Molecules 26, no. 19: 6039. https://doi.org/10.3390/molecules26196039

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