Harrowven, D. C., Nunn, M. I. T., Blumire, N. J. and Fenwick, D. R.
A total synthesis of toddaquinoline exposes a dual role for cobalt in radical additions to pyridines
Tetrahedron Letters, 41, (34), . (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.
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