A total synthesis of toddaquinoline exposes a dual role for cobalt in radical additions to pyridines
A total synthesis of toddaquinoline exposes a dual role for cobalt in radical additions to pyridines
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.
radicals and radical reactions, natural products, polycyclic
heterocyclic compounds, cobalt and its compounds, photochemistry, pyridines
6681-6683
Harrowven, D. C.
1c293b83-4291-4301-a7a4-167d6a146d01
Nunn, M. I. T.
b8208d55-5e1b-45fb-a1cc-8e1df72d6b2d
Blumire, N. J.
0db582c0-d202-4646-8048-5297fa0afc91
Fenwick, D. R.
6021f20e-6a22-41c6-bc2d-67c4ea2f8d59
19 August 2000
Harrowven, D. C.
1c293b83-4291-4301-a7a4-167d6a146d01
Nunn, M. I. T.
b8208d55-5e1b-45fb-a1cc-8e1df72d6b2d
Blumire, N. J.
0db582c0-d202-4646-8048-5297fa0afc91
Fenwick, D. R.
6021f20e-6a22-41c6-bc2d-67c4ea2f8d59
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), .
(doi:10.1016/S0040-4039(00)01119-9).
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.
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Published date: 19 August 2000
Keywords:
radicals and radical reactions, natural products, polycyclic
heterocyclic compounds, cobalt and its compounds, photochemistry, pyridines
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Local EPrints ID: 18847
URI: http://eprints.soton.ac.uk/id/eprint/18847
ISSN: 0040-4039
PURE UUID: 485242e2-5b58-4d53-aba2-563b196ba1b6
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Date deposited: 12 Dec 2005
Last modified: 15 Mar 2024 06:08
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Author:
D. C. Harrowven
Author:
M. I. T. Nunn
Author:
N. J. Blumire
Author:
D. R. Fenwick
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