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New insights into cyclobutenone rearrangements: a total synthesis of the natural ROS-generating anti-cancer agent cribrostatin 6

New insights into cyclobutenone rearrangements: a total synthesis of the natural ROS-generating anti-cancer agent cribrostatin 6
New insights into cyclobutenone rearrangements: a total synthesis of the natural ROS-generating anti-cancer agent cribrostatin 6
Aryl- and heteroarylcyclobutenone rearrangements proceed in excellent yield under continuous-flow conditions. The former shows a Hammett correlation with ?I providing strong evidence that electrocyclisation is the rate-determining step and has a late transition state. The reaction has been modelled by using DFT and CCSD(T) methods, with the latter giving excellent correlation with the experimental rate constant. A short and efficient total synthesis of cribrostatin?6, an anti-neoplastic and anti-microbial agent, provides a topical demonstration of the value of this method.
density functional calculations, flow chemistry, hammett correlation, reaction mechanisms, thermochemistry
0947-6539
13698-13705
Mohamed, Mubina
f564fdda-ede9-49b8-8689-2e9fe1a90fa8
Gonçalves, Théo P.
bf763652-dc7b-4f8e-9cc2-6be930274533
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
Sneddon, Helen F.
33850179-8489-433a-b8c9-09536a4e2b18
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Mohamed, Mubina
f564fdda-ede9-49b8-8689-2e9fe1a90fa8
Gonçalves, Théo P.
bf763652-dc7b-4f8e-9cc2-6be930274533
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
Sneddon, Helen F.
33850179-8489-433a-b8c9-09536a4e2b18
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b

Mohamed, Mubina, Gonçalves, Théo P., Whitby, Richard J., Sneddon, Helen F. and Harrowven, David C. (2011) New insights into cyclobutenone rearrangements: a total synthesis of the natural ROS-generating anti-cancer agent cribrostatin 6. Chemistry - A European Journal, 17 (49), 13698-13705. (doi:10.1002/chem.201102263).

Record type: Article

Abstract

Aryl- and heteroarylcyclobutenone rearrangements proceed in excellent yield under continuous-flow conditions. The former shows a Hammett correlation with ?I providing strong evidence that electrocyclisation is the rate-determining step and has a late transition state. The reaction has been modelled by using DFT and CCSD(T) methods, with the latter giving excellent correlation with the experimental rate constant. A short and efficient total synthesis of cribrostatin?6, an anti-neoplastic and anti-microbial agent, provides a topical demonstration of the value of this method.

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e-pub ahead of print date: 14 November 2011
Published date: 2 December 2011
Keywords: density functional calculations, flow chemistry, hammett correlation, reaction mechanisms, thermochemistry
Organisations: Chemistry

Identifiers

Local EPrints ID: 337266
URI: http://eprints.soton.ac.uk/id/eprint/337266
ISSN: 0947-6539
PURE UUID: 91d4d6b9-03af-4b23-a4cf-812a86492c4a
ORCID for Richard J. Whitby: ORCID iD orcid.org/0000-0002-9891-5502
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

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Date deposited: 20 Apr 2012 12:26
Last modified: 18 Feb 2021 16:43

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Contributors

Author: Mubina Mohamed
Author: Théo P. Gonçalves
Author: Helen F. Sneddon

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