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A novel strategy is described in which an intermolecular carbon-centered radical addition to a β-oxygenated acceptor followed by intramolecular cyclization leads to the formation of 2,3,4- and 2,3,4,5-substituted furan rings. Excellent levels of 2,4-trans selectivity are observed in accordance with the Beckwith-Houk model for selectivity in 5-exo radical cyclizations.
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