Effect of tether length on endo/exo stereoselectivity in alkene–arene meta‐photocycloaddition reactions towards the Aphidocolin/Stemodin scaffolds

[thumbnail of Open Access]
Preview
Text (Open Access) - Published Version
· Available under License Creative Commons Attribution.
· Please see our End User Agreement before downloading.
| Preview
Available under license: Creative Commons Attribution
[thumbnail of A Alkene-Arene meta-Cycloaddition - Manuscript.pdf]
Text - Accepted Version
· Restricted to Repository staff only
Restricted to Repository staff only
[thumbnail of SI with experimental procedures and spectra]
Preview
Text (SI with experimental procedures and spectra) - Supplemental Material
· Please see our End User Agreement before downloading.
| Preview

Please see our End User Agreement.

It is advisable to refer to the publisher's version if you intend to cite from this work. See Guidance on citing.

Add to AnyAdd to TwitterAdd to FacebookAdd to LinkedinAdd to PinterestAdd to Email

Alshammari, A. A. A., Boyd, J. W., Greaves, N., Kettle, J. G., McKendrick, J. E. orcid id iconORCID: https://orcid.org/0000-0003-2275-0569, Parker, L. G., Russell, A. T., Sani, A. and Smith, C. D. orcid id iconORCID: https://orcid.org/0000-0002-5911-5836 (2024) Effect of tether length on endo/exo stereoselectivity in alkene–arene meta‐photocycloaddition reactions towards the Aphidocolin/Stemodin scaffolds. European Journal of Organic Chemistry, 27 (30). e202400463. ISSN 1099-0690 doi: 10.1002/ejoc.202400463

Abstract/Summary

Intramolecular alkene-arene meta-photocycloadditions are powerful transformations that use the enhanced reactivity of photoexcited benzene rings to facilitate addition of an alkene 1,3 across donor groups and form complex three-dimensional fused-ring systemsfrom readily accessible starting materials. Intramolecular examples havetraditionallybeen restricted to 3-memberedtethers, with cycloaddition resulting from exo-conformation. However, by judicious tether design we have demonstratedthat a 4-membered tether can also proceed in good yield; interestingly,viaan endo-exciplex(1.2:1) enabling access to both natural product skeletons and interesting scaffolds for medicinal chemistry research.

Altmetric Badge

Item Type Article
URI https://reading-clone.eprints-hosting.org/id/eprint/116221
Identification Number/DOI 10.1002/ejoc.202400463
Refereed Yes
Divisions Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Mass Spectrometry (CAF)
Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > NMR (CAF)
Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Optical Spectroscopy (CAF)
Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Xray (CAF)
Uncontrolled Keywords meta-Photocycloaddition; Photochemistry; Aphidicolin; Stemodin; Flow
Publisher European Chemical Societies Publishing
Download/View statistics View download statistics for this item

Downloads

Downloads per month over past year

University Staff: Request a correction | Centaur Editors: Update this record

Search Google Scholar