The first total synthesis of toddaquinoline, an alkaloid from Toddalia asiatica
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).
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Description/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.
| Item Type: | Article |
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| Related URLs: | |
| 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 |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 19505 |
| Date Deposited: | 14 Feb 2006 |
| Last Modified: | 01 Apr 2012 00:57 |
| Contributors: | Harrowven, D. C. (Author) Nunn, M. I. T. (Author) Blumire, N. J. (Author) Fenwick, D. R. (Author) |
| Date: | 14 May 2001 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/19505 |
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