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A total synthesis of toddaquinoline exposes a dual role for cobalt in radical additions to pyridines

✍ Scribed by David C Harrowven; Michael I.T Nunn; Nigel J Blumire; David R Fenwick

Book ID
104210715
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
118 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

This paper describes the ®rst 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: ®rstly 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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