The first total synthesis of toddaquinoline, an alkaloid from Toddalia asiatica
The first total synthesis of toddaquinoline, an alkaloid from Toddalia asiatica
The paper describes the first total synthesis of toddaquinoline, an alkaloid from the root bark of Formosan Toddalia asiatica. The key step is cobalt(I) mediated radial cyclisation to a pyridine. Cobalt appears to play a dual role in the reaction, firstly initialising homolysis of the carbon to halogen bond then acting as a Lewis acid to promote cyclisation to C-6. Other approaches examined are also outlined. These include a photocyclisation of an azastilbene; a cyclisation induced by halogen to metal exchange and a tin mediated radical cyclisation.
radicals and radical reactions, natural products, polycyclic
heterocyclic compounds, cobalt and its compounds, photochemistry, pyridinescascade radical reactions, condensed thiophenes, pyridinium rings, sequence, ketenethioacetals, substitution, indanes
4447-4454
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
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
14 May 2001
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
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.
(2001)
The first total synthesis of toddaquinoline, an alkaloid from Toddalia asiatica.
Tetrahedron, 57 (20), .
(doi:10.1016/S0040-4020(01)00336-2).
Abstract
The paper describes the first total synthesis of toddaquinoline, an alkaloid from the root bark of Formosan Toddalia asiatica. The key step is cobalt(I) mediated radial cyclisation to a pyridine. Cobalt appears to play a dual role in the reaction, firstly initialising homolysis of the carbon to halogen bond then acting as a Lewis acid to promote cyclisation to C-6. Other approaches examined are also outlined. These include a photocyclisation of an azastilbene; a cyclisation induced by halogen to metal exchange and a tin mediated radical cyclisation.
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Published date: 14 May 2001
Keywords:
radicals and radical reactions, natural products, polycyclic
heterocyclic compounds, cobalt and its compounds, photochemistry, pyridinescascade radical reactions, condensed thiophenes, pyridinium rings, sequence, ketenethioacetals, substitution, indanes
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Local EPrints ID: 19505
URI: http://eprints.soton.ac.uk/id/eprint/19505
ISSN: 0040-4020
PURE UUID: 626b1e8b-ed83-40e4-aba7-d2482456e417
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Date deposited: 14 Feb 2006
Last modified: 16 Mar 2024 02:46
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Author:
M. I. T. Nunn
Author:
N. J. Blumire
Author:
D. R. Fenwick
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