title: Synthesis of oxepanes and trans-fused bisoxepanes via biomimetic, endo-regioselective tandem oxacyclizations of polyepoxides.
abstract: [reaction: see text] This communication describes the first examples of tandem endo-regioselective and stereospecific oxacyclizations of 1, 5-diepoxides to oxepane products and a similar tandem oxacyclization of 1,5,9-triepoxides to fused bisoxepane cyclic carbonates. A mechanism for these biomimetic oxacyclizations is proposed in which the epoxides act as both electrophilic and nucleophilic reaction partners.
authors.affiliation: Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, Georgia 30322, USA. fmcdona@emory.edu
authors.forename: F E
authors.initials: FE
authors.lastname: McDonald
authors.forename: X
authors.initials: X
authors.lastname: Wang
authors.forename: B
authors.initials: B
authors.lastname: Do
authors.forename: K I
authors.initials: KI
authors.lastname: Hardcastle
mesh_terms: D004852:Epoxy Compounds / Q000138:chemical synthesis*; D008387:Marine Toxins / Q000138:chemical synthesis; D018716:Molecular Mimicry; D010082:Oxepins / Q000138:chemical synthesis*; D011083:Polycyclic Compounds / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D008387:Marine Toxins; D010082:Oxepins; D011083:Polycyclic Compounds