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Pure Appl. Chem., 2007, Vol. 79, No. 2, pp. 281-291

Biomimetic synthesis via polyepoxide cyclizations

Frank E. McDonald, Rongbiao Tong, Jason C. Valentine and Fernando Bravo

Department of Chemistry, Emory University, Atlanta, GA 30322, USA

Abstract: The biomimetic synthesis of trans,syn,trans-fused polycyclic ether natural products involving a cascade of stereospecific and regioselective oxacyclizations of polyepoxide substrates is described as applied to the synthesis of polyoxepane and polypyran structures. In addition, an extension of biomimetic polyene cyclizations to terpenoid natural products is outlined.