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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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.
|Digital Object Identifier (DOI):||doi:10.1016/S0040-4039(00)01119-9|
|Keywords:||radicals and radical reactions, natural products, polycyclic heterocyclic compounds, cobalt and its compounds, photochemistry, pyridines|
Q Science > QD Chemistry
|Divisions:||University Structure - Pre August 2011 > School of Chemistry
|Date Deposited:||12 Dec 2005|
|Last Modified:||06 Aug 2015 02:18|
|RDF:||RDF+N-Triples, RDF+N3, RDF+XML, Browse.|
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