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

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Johnston_2021_Synthesis_of_indoloquinolines_Molecules_26_06039_CC.pdf (880.8Kb)
Date
05/10/2021
Author
Johnston, Craig A.
Cordes, David Bradford
Lebl, Tomas
Slawin, Alexandra Martha Zoya
Westwood, Nicholas James
Keywords
Intramolecular cyclization
X-ray structure
Perophoramidine
Natural product
Claisen rearrangement
Indoloquinoline
QD Chemistry
DAS
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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.
Citation
Johnston , C A , Cordes , D B , Lebl , T , Slawin , A M Z & Westwood , N J 2021 , ' Synthesis of indoloquinolines : an intramolecular cyclization leading to advanced Perophoramidine-relevant intermediates ' , Molecules , vol. 26 , no. 19 , 6039 . https://doi.org/10.3390/molecules26196039
Publication
Molecules
Status
Peer reviewed
DOI
https://doi.org/10.3390/molecules26196039
ISSN
1420-3049
Type
Journal article
Rights
Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Description
We thank EPSRC (UK) for a DTA studentship for C.A.J.
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  • University of St Andrews Research
URL
https://www.mdpi.com/1420-3049/26/19/6039
https://www.mdpi.com/journal/molecules/special_issues/Alexandra_Slawin
URI
http://hdl.handle.net/10023/24094

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