title: Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids--first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (-)-trans-dihydroxygirinimbine.
abstract: Iron-mediated oxidative cyclisation provides an efficient approach to pyrano[3,2-a]carbazole alkaloids. Thus, improved routes to girinimbine and murrayacine as well as the first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine are reported. Asymmetric epoxidation of girinimbine led to (-)-trans-dihydroxygirinimbine and the assignment of its absolute configuration.
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.
authors.forename: Konstanze K
authors.initials: KK
authors.lastname: Gruner
authors.forename: Thomas
authors.initials: T
authors.lastname: Hopfmann
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Matsumoto
authors.forename: Anne
authors.initials: A
authors.lastname: Jäger
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Katsuki
authors.forename: Hans-Joachim
authors.initials: HJ
authors.lastname: Knölker
mesh_terms: D000470:Alkaloids; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D007501:Iron / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C558546:7-methoxymurrayacine; D000470:Alkaloids; D002227:Carbazoles; D004852:Epoxy Compounds; C558545:O-methylmurrayamine A; C558547:trans-dihydroxygirinimbine; D007501:Iron