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Synfacts 2008(12): 1309-1309  
DOI: 10.1055/s-0028-1087326
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Oxidative Aromatic Umpolung Strategy Applied to Tetrahydrofuran Synthesis

Contributor(s): Mark Lautens, Frédéric Ménard
C. Sabot, D. Bérard, S. Canesi*
Université du Québec à Montréal, Canada
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Publication History

Publication Date:
20 November 2008 (online)

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Significance

Two substrates that are typically strong nucleophiles are joined by an oxidative Umpolung reaction. The natural reactivity of phenol is reversed by its oxidation with diacetatoiodobenzene (DIB) and is made into an electrophilic cationic intermediate. The oxidative formal [3+2] cyclization yields a fused bis(dihydrofuran) product regio- and diastereoselectively in one operation. The power of the transformation was demonstrated by impressively short syntheses of panacene and some analogues.