Synthesis of oxepanes and trans-fused bisoxepanes via biomimetic, endo-regioselective tandem oxacyclizations of polyepoxides.
[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.
McDonald
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Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, Georgia 30322, USA. fmcdona@emory.edu
Wang
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Do
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Hardcastle
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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
D004852:Epoxy Compounds; D008387:Marine Toxins; D010082:Oxepins; D011083:Polycyclic Compounds