The use of temporary tethers in the meta photocycloaddition reaction

Penkett, Clive S, Byrne, Paul W, Teobald, Barry J, Rola, Benedicte, Ozanne, Aurelie and Hitchcock, Peter B (2004) The use of temporary tethers in the meta photocycloaddition reaction. Tetrahedron, 60 (12). pp. 2771-2784. ISSN 0040-4020

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Abstract

The use of temporary tethers in facilitating meta photocycloaddition reactions between phenol and allyl alcohol derivatives has been investigated. The merits of silicon, carbonate and methylene acetal tethers were assessed, whilst considering strategies for the preparation of the natural products gymnomitrol and gelsemine. The photoadducts were epoxidised, and then subjected to acid catalysed fragmentation with concomitant cleavage of the tether. Depending on whether water or methanol was used during the fragmentation stage of the methylene tethers. the methylene group was either removed altogether or transformed into a MOM group.

Item Type: Article
Additional Information: CSP directed the work and is the corresponding author. Paper describes the novel application of various tethers in controlling the synthetically important meta photocycloaddition reaction. Novel routes to the synthesis of various natural product frameworks were developed.
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Clive Penkett
Date Deposited: 06 Feb 2012 21:28
Last Modified: 30 Mar 2012 13:08
URI: http://sro.sussex.ac.uk/id/eprint/31349
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