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).

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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
Digital Object Identifier (DOI): doi:10.1016/S0040-4039(00)01119-9
ISSNs: 0040-4039 (print)
Keywords: radicals and radical reactions, natural products, polycyclic heterocyclic compounds, cobalt and its compounds, photochemistry, pyridines
Subjects:
ePrint ID: 18847
Date :
Date Event
19 August 2000Published
Date Deposited: 12 Dec 2005
Last Modified: 16 Apr 2017 23:08
Further Information:Google Scholar
URI: http://eprints.soton.ac.uk/id/eprint/18847

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