title: Epoxide Opening of a 7,17-Seco-7,8-Epoxy-C19-Diterpenoid Alkaloid.
abstract: A new and effective approach toward epoxide opening of a 7,17-seco-7,8-epoxy-C19-diterpenoid alkaloid is herein described. The starting epoxide was prepared from naturally occurring yunnaconitine via a nine-step transformation. Treatment of this epoxide with trifluoroacetic anhydride in dioxane at 110 degrees C followed by reduction with sodium boron hydride generated two epoxide opening compounds 7 and 8. Each of their structures is characteristic of a Δ8,15 bridgehead double bond and a 7β-oxygen-substituted group.
authors.forename: Hong
authors.initials: H
authors.lastname: Ji
authors.forename: Feng-Peng
authors.initials: FP
authors.lastname: Wang
authors.forename: Qiao-Hong
authors.initials: QH
authors.lastname: Chen
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000470:Alkaloids; D004224:Diterpenes; D004852:Epoxy Compounds; C000606170:yunnacontine