title: Synthesis of vinca alkaloids and related compounds. 100. Stereoselective oxidation reactions of compounds with the aspidospermane and quebrachamine ring system. First synthesis of some alkaloids containing the epoxy ring.
abstract: The first syntheses of the alkaloids (-)-mehranine (3), (+)-voaphylline/conoflorine (4), (+)-N(a)-methylvoaphylline/hecubine (5), and (-)-lochnericine (2) were achieved by stereoselective epoxidation starting from (-)-tabersonine (1), through intermediates with the aspidospermane and quebrachamine skeleton.
authors.affiliation: Department for Organic Chemistry, Budapest University of Technology and Economics, Gellért tér 4, H-1111, Budapest, Hungary.
authors.forename: János
authors.initials: J
authors.lastname: Eles
authors.forename: György
authors.initials: G
authors.lastname: Kalaus
authors.forename: István
authors.initials: I
authors.lastname: Greiner
authors.forename: Mária
authors.initials: M
authors.lastname: Kajtár-Peredy
authors.forename: Pál
authors.initials: P
authors.lastname: Szabó
authors.forename: György Miklós
authors.initials: GM
authors.lastname: Keserû
authors.forename: Lajos
authors.initials: L
authors.lastname: Szabó
authors.forename: Csaba
authors.initials: C
authors.lastname: Szántay
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011804:Quinolines; D013237:Stereoisomerism; D014748:Vinca Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles; D011804:Quinolines; D014748:Vinca Alkaloids; C091897:quebrachamine; C091896:aspidospermine