title: Total synthesis of ent-dioxepandehydrothyrsiferol via a bromonium-initiated epoxide-opening cascade.
abstract: 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.
authors: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
authors: Jessica
authors: J
authors: Tanuwidjaja
authors: Sze-Sze
authors: SS
authors: Ng
authors: Timothy F
authors: TF
authors: Jamison
mesh_terms: D001966:Bromine / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D005240:Feasibility Studies; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D004852:Epoxy Compounds; D006575:Heterocyclic Compounds, 3-Ring; C545060:dioxepandehydrothyrsiferol; D001966:Bromine