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The first total synthesis of toddaquinoline, an alkaloid from Toddalia asiatica

The first total synthesis of toddaquinoline, an alkaloid from Toddalia asiatica
The first total synthesis of toddaquinoline, an alkaloid from Toddalia asiatica
The paper describes the first total synthesis of toddaquinoline, an alkaloid from the root bark of Formosan Toddalia asiatica. The key step is cobalt(I) mediated radial cyclisation to a pyridine. Cobalt appears to play a dual role in the reaction, firstly initialising homolysis of the carbon to halogen bond then acting as a Lewis acid to promote cyclisation to C-6. Other approaches examined are also outlined. These include a photocyclisation of an azastilbene; a cyclisation induced by halogen to metal exchange and a tin mediated radical cyclisation.
radicals and radical reactions, natural products, polycyclic heterocyclic compounds, cobalt and its compounds, photochemistry, pyridinescascade radical reactions, condensed thiophenes, pyridinium rings, sequence, ketenethioacetals, substitution, indanes
0040-4020
4447-4454
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Nunn, M. I. T.
b8208d55-5e1b-45fb-a1cc-8e1df72d6b2d
Blumire, N. J.
0db582c0-d202-4646-8048-5297fa0afc91
Fenwick, D. R.
6021f20e-6a22-41c6-bc2d-67c4ea2f8d59
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Nunn, M. I. T.
b8208d55-5e1b-45fb-a1cc-8e1df72d6b2d
Blumire, N. J.
0db582c0-d202-4646-8048-5297fa0afc91
Fenwick, D. R.
6021f20e-6a22-41c6-bc2d-67c4ea2f8d59

Harrowven, D. C., Nunn, M. I. T., Blumire, N. J. and Fenwick, D. R. (2001) The first total synthesis of toddaquinoline, an alkaloid from Toddalia asiatica. Tetrahedron, 57 (20), 4447-4454. (doi:10.1016/S0040-4020(01)00336-2).

Record type: Article

Abstract

The paper describes the first total synthesis of toddaquinoline, an alkaloid from the root bark of Formosan Toddalia asiatica. The key step is cobalt(I) mediated radial cyclisation to a pyridine. Cobalt appears to play a dual role in the reaction, firstly initialising homolysis of the carbon to halogen bond then acting as a Lewis acid to promote cyclisation to C-6. Other approaches examined are also outlined. These include a photocyclisation of an azastilbene; a cyclisation induced by halogen to metal exchange and a tin mediated radical cyclisation.

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More information

Published date: 14 May 2001
Keywords: radicals and radical reactions, natural products, polycyclic heterocyclic compounds, cobalt and its compounds, photochemistry, pyridinescascade radical reactions, condensed thiophenes, pyridinium rings, sequence, ketenethioacetals, substitution, indanes

Identifiers

Local EPrints ID: 19505
URI: http://eprints.soton.ac.uk/id/eprint/19505
ISSN: 0040-4020
PURE UUID: 626b1e8b-ed83-40e4-aba7-d2482456e417
ORCID for D. C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

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Date deposited: 14 Feb 2006
Last modified: 16 Mar 2024 02:46

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Contributors

Author: D. C. Harrowven ORCID iD
Author: M. I. T. Nunn
Author: N. J. Blumire
Author: D. R. Fenwick

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