Total Synthesis of ent-Dioxepandehydrothyrsiferol via a Bromonium-Initiated Epoxide-Opening Cascade
Author(s)Tanuwidjaja, Jessica; Ng, Sze-Sze; Jamison, Timothy F.
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In the first total synthesis of ent-dioxepandehydrothyrsiferol, the signature trans-anti-trans 7,7,6-fused tricyclic polyether framework was constructed in a single bromonium-initiated epoxide-opening cascade that incorporates both endo- and exo-selective epoxide openings, each directed by the substitution pattern of the epoxide (methyl groups). This study thus demonstrates the feasibility of a possible biogenesis.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Journal of the American Chemical Society
American Chemical Society (ACS)
Tanuwidjaja, Jessica, Sze-Sze Ng, and Timothy F. Jamison. “Total Synthesis of ent-Dioxepandehydrothyrsiferol via a Bromonium-Initiated Epoxide-Opening Cascade.” Journal of the American Chemical Society 131, no. 34 (September 2, 2009): 12084-12085.
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