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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), pp. 6681-6683. (doi:10.1016/S0040-4039(00)01119-9).

Record type: Article

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.

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Published date: 19 August 2000
Keywords: radicals and radical reactions, natural products, polycyclic heterocyclic compounds, cobalt and its compounds, photochemistry, pyridines

Identifiers

Local EPrints ID: 18847
URI: http://eprints.soton.ac.uk/id/eprint/18847
ISSN: 0040-4039
PURE UUID: 485242e2-5b58-4d53-aba2-563b196ba1b6

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Date deposited: 12 Dec 2005
Last modified: 17 Jul 2017 16:34

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Contributors

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

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