title: Investigating Biogenetic Hypotheses of the Securinega Alkaloids: Enantioselective Total Syntheses of Secu'amamine E/ent-Virosine A and Bubbialine.
abstract: The synthesis of the Securinega alkaloid secu'amamine E (ent-virosine A) has been accomplished for the first time in 12 steps and 8.5% overall yield. In addition, bubbialine has been prepared and characterized. These two alkaloids and bubbialidine, all featuring an azabicyclo[2.2.2]octane core, were rearranged to their azabicyclo[3.2.1]octane congeners, a framework found in many Securinega alkaloids. These experiments suggest that azabicyclo[2.2.2]octane derivatives could serve as intermediates in the biosynthesis of the rearranged azabicyclo[3.2.1]octane products.
authors.affiliation: Department of Chemistry, University of Zurich , 8057 Zurich, Switzerland.|Department of Chemistry, University of Basel , 4056 Basel, Switzerland.
authors.forename: Robin
authors.initials: R
authors.lastname: Wehlauch
authors.affiliation: Department of Chemistry, University of Zurich , 8057 Zurich, Switzerland.
authors.forename: Simone M
authors.initials: SM
authors.lastname: Grendelmeier
authors.affiliation: Department of Chemistry, University of Basel , 4056 Basel, Switzerland.
authors.forename: Hideki
authors.initials: H
authors.lastname: Miyatake-Ondozabal
authors.affiliation: Department of Chemistry, University of Basel , 4056 Basel, Switzerland.
authors.forename: Alexander H
authors.initials: AH
authors.lastname: Sandtorv
authors.affiliation: Department of Chemistry, University of Zurich , 8057 Zurich, Switzerland.|Department of Chemistry, University of Basel , 4056 Basel, Switzerland.
authors.forename: Manuel
authors.initials: M
authors.lastname: Scherer
authors.affiliation: Department of Chemistry, University of Zurich , 8057 Zurich, Switzerland.
authors.forename: Karl
authors.identifier: 0000-0003-3053-0689
authors.initials: K
authors.lastname: Gademann
mesh_terms: D000470:Alkaloids; D019665:Euphorbiaceae / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C574406:virosine A