The University of Southampton
University of Southampton Institutional Repository

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
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
0040-4039
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
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), 6681-6683. (doi:10.1016/S0040-4039(00)01119-9).

Record type: Article

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.

Full text not available from this repository.

More information

Published date: 19 August 2000
Keywords: radicals and radical reactions, natural products, polycyclic heterocyclic compounds, cobalt and its compounds, photochemistry, pyridines

Identifiers

Local EPrints ID: 18847
URI: http://eprints.soton.ac.uk/id/eprint/18847
ISSN: 0040-4039
PURE UUID: 485242e2-5b58-4d53-aba2-563b196ba1b6

Catalogue record

Date deposited: 12 Dec 2005
Last modified: 15 Jul 2019 19:28

Export record

Altmetrics

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×