title: A Route to the C,D,E Ring System of the Aspidosperma Alkaloids.
abstract: A short synthetic sequence leading to the formation of the C,D,E-ring subunit of the Aspidosperma alkaloids is reported. This route is based on a ring fragmentation/intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction sequence that gives the desired tricyclic product as a single diastereomer. A γ-amino-β-hydroxy-α-diazo carbonyl compound is shown to fragment in the presence of a Lewis acid to give an iminium product that can be directly reduced to the corresponding amine.
authors: Department of Chemistry, The University of Vermont , Burlington, Vermont 05405, United States.
authors: Geoffrey M
authors: GM
authors: Giampa
authors: Department of Chemistry, The University of Vermont , Burlington, Vermont 05405, United States.
authors: Jian
authors: J
authors: Fang
authors: Department of Chemistry, The University of Vermont , Burlington, Vermont 05405, United States.
authors: Matthias
authors: M
authors: Brewer
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D030009:Aspidosperma / Q000737:chemistry*; D008968:Molecular Conformation
chemical_list: D000470:Alkaloids