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

Record type: Article

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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Citation

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), pp. 4447-4454. (doi:10.1016/S0040-4020(01)00336-2).

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

Catalogue record

Date deposited: 14 Feb 2006
Last modified: 17 Jul 2017 16:31

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Contributors

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

University divisions


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