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.
Keywords: biomimetic synthesis; polycyclic ethers; polyepoxides; tandem cyclizations; polycyclic terpenes.
*Paper based on a presentation at the 16th International Conference on Organic Synthesis (ICOS-16), 11-15 June 2006, Mérida, Yucatán, México. Other presentations are published in this issue, pp. 153-291.