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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 Hitchcock
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.

History

Publication status

  • Published

Journal

Tetrahedron

ISSN

0040-4020

Publisher

Elsevier

Issue

12

Volume

60

Page range

2771-2784

Pages

14.0

Department 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

2012-02-06

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