SmI2–H2O-mediated 5-exo/6-exo lactone radical cyclisation cascades

Irem Yalavac; Sarah E. Lyons; Michael R. Webb; David J. Procter

doi:10.1039/C4CC05404K

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SmI₂–H₂O-mediated 5-exo/6-exo lactone radical cyclisation cascades†

Irem Yalavac,^a Sarah E. Lyons,^a Michael R. Webb^b and David J. Procter*^a

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* Corresponding authors

^a School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK
E-mail: david.j.procter@manchester.ac.uk

^b Medicines Research Centre, GlaxoSmithKline, Gunnels Wood Road, Stevenage, Herts, SG1 2NY, UK

Abstract

The SmI₂–H₂O reagent system mediates challenging 5-exo/6-exo lactone radical cascade cyclisations that deliver carbo[5.4.0]bicyclic motifs in a diastereoselective, one-pot process that establish two new carbocyclic rings and four stereocentres.

This article is part of the themed collection: In Celebration of Richard Taylor’s 65th Birthday

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Article information

DOI: https://doi.org/10.1039/C4CC05404K
Article type: Communication
Submitted: 14 Jul 2014
Accepted: 15 Aug 2014
First published: 15 Aug 2014

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Chem. Commun., 2014,50, 12863-12866

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SmI₂–H₂O-mediated 5-exo/6-exo lactone radical cyclisation cascades

I. Yalavac, S. E. Lyons, M. R. Webb and D. J. Procter, Chem. Commun., 2014, 50, 12863 DOI: 10.1039/C4CC05404K

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