The first total synthesis of toddaquinoline, an alkaloid from Toddalia asiatica


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), 4447-4454. (doi:10.1016/S0040-4020(01)00336-2).

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Description/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.

Item Type: Article
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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
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 19505
Date Deposited: 14 Feb 2006
Last Modified: 27 Mar 2014 18:09
URI: http://eprints.soton.ac.uk/id/eprint/19505

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