A total synthesis of toddaquinoline exposes a dual role for cobalt in radical additions to pyridines
Harrowven, D. C., Nunn, M. I. T., Blumire, N. J. and Fenwick, D. R. (2000) A total synthesis of toddaquinoline exposes a dual role for cobalt in radical additions to pyridines. Tetrahedron Letters, 41, (34), 6681-6683. (doi:10.1016/S0040-4039(00)01119-9).
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Description/Abstract
This paper describes the first total synthesis of toddaquinoline, an alkaloid from the root bark of Formosan Toddalia asiatica. importantly, the synthesis has exposed a dichotomy in radical reactions mediated by tin and cobalt(I) that involve additions to pyridines. Our observations suggest that cobalt plays a dual role in such reactions: firstly initiating homolysis of the carbon to halogen bond, then acting as a Lewis acid to promote radical additions to the carbon centre adjacent to nitrogen.
| Item Type: | Article |
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| Related URLs: | |
| Keywords: | radicals and radical reactions, natural products, polycyclic heterocyclic compounds, cobalt and its compounds, photochemistry, pyridines |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 18847 |
| Date Deposited: | 12 Dec 2005 |
| Last Modified: | 01 Jun 2011 06:11 |
| Contributors: | Harrowven, D. C. (Author) Nunn, M. I. T. (Author) Blumire, N. J. (Author) Fenwick, D. R. (Author) |
| Date: | 19 August 2000 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/18847 |
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