Tetrahedron Letters p. 6681 - 6683 (2000)
Update date:2022-08-11
Topics:
Harrowven
Nunn
Blumire
Fenwick
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. (C) 2000 Elsevier Science Ltd.
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