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

Craig A. Johnston; David Bradford Cordes; Tomas Lebl; Alexandra Martha Zoya Slawin; Nicholas James Westwood

doi:10.3390/molecules26196039

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

Craig A. Johnston, David Bradford Cordes, Tomas Lebl, Alexandra Martha Zoya Slawin, Nicholas James Westwood

Research output: Contribution to journal › Article › peer-review

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 language	English
Article number	6039
Number of pages	19
Journal	Molecules
Volume	26
Issue number	19
DOIs	https://doi.org/10.3390/molecules26196039
Publication status	Published - 5 Oct 2021

Keywords

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

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10.3390/molecules26196039Licence: CC BY

Johnston-2021-Synthesis-of-indoloquinolines-Molecules-26-06039-CC
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/).
Final published version, 881 KBLicence: CC BY

Cite this

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title = "Synthesis of indoloquinolines: an intramolecular cyclization leading to advanced Perophoramidine-relevant intermediates",

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.",

keywords = "Intramolecular cyclization, X-ray structure, Perophoramidine, Natural product, Claisen rearrangement, Indoloquinoline",

author = "Johnston, {Craig A.} and Cordes, {David Bradford} and Tomas Lebl and Slawin, {Alexandra Martha Zoya} and Westwood, {Nicholas James}",

note = "We thank EPSRC (UK) for a DTA studentship for C.A.J.",

year = "2021",

month = oct,

day = "5",

doi = "10.3390/molecules26196039",

language = "English",

volume = "26",

journal = "Molecules",

issn = "1420-3049",

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TY - JOUR

T1 - Synthesis of indoloquinolines

T2 - an intramolecular cyclization leading to advanced Perophoramidine-relevant intermediates

AU - Johnston, Craig A.

AU - Cordes, David Bradford

AU - Lebl, Tomas

AU - Slawin, Alexandra Martha Zoya

AU - Westwood, Nicholas James

N1 - We thank EPSRC (UK) for a DTA studentship for C.A.J.

PY - 2021/10/5

Y1 - 2021/10/5

N2 - 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.

AB - 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.

KW - Intramolecular cyclization

KW - X-ray structure

KW - Perophoramidine

KW - Natural product

KW - Claisen rearrangement

KW - Indoloquinoline

UR - https://www.mdpi.com/1420-3049/26/19/6039

UR - https://www.mdpi.com/journal/molecules/special_issues/Alexandra_Slawin

U2 - 10.3390/molecules26196039

DO - 10.3390/molecules26196039

M3 - Article

SN - 1420-3049

VL - 26

JO - Molecules

JF - Molecules

IS - 19

M1 - 6039

ER -

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

Abstract

Keywords

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CCDC 2109434 & 2109435: Experimental Crystal Structure Determination

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

Abstract

Keywords

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Datasets

CCDC 2109434 & 2109435: Experimental Crystal Structure Determination

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