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The use of temporary tethers in the meta photocycloaddition reaction
journal contribution
posted on 2023-06-08, 10:04 authored by Clive S Penkett, Paul W Byrne, Barry J Teobald, Benedicte Rola, Aurelie Ozanne, Peter B HitchcockThe 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.
History
Publication status
- Published
Journal
TetrahedronISSN
0040-4020Publisher
ElsevierExternal DOI
Issue
12Volume
60Page range
2771-2784Pages
14.0Department affiliated with
- Chemistry Publications
Notes
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.Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2012-02-06Usage metrics
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