title: Synthesis of Methylene-Bridged Biscarbazole Alkaloids by using an Ullmann-type Coupling: First Total Synthesis of Murrastifoline-C and Murrafoline-E.
abstract: We describe the total synthesis of methylene-bridged biscarbazole alkaloids by using a late-stage Ullmann-type coupling of fully functionalised carbazole subunits. The carbazole derivatives were synthesised via a sequence of palladium(0)- and palladium(II)-catalysed coupling reactions. Our approach has provided bismurrayafoline-A, bismurrayafolinol, chrestifolines B-D, and the first total synthesis of murrastifoline-C and murrafoline-E.
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069, Dresden, Germany), Fax.
authors.forename: Sebastian K
authors.initials: SK
authors.lastname: Kutz
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069, Dresden, Germany), Fax.
authors.forename: Carsten
authors.initials: C
authors.lastname: Börger
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069, Dresden, Germany), Fax.
authors.forename: Arndt W
authors.initials: AW
authors.lastname: Schmidt
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069, Dresden, Germany), Fax. hans-joachim.knoelker@tu-dresden.de.
authors.forename: Hans-Joachim
authors.initials: HJ
authors.lastname: Knölker
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D002227:Carbazoles; D006576:Heterocyclic Compounds, 4 or More Rings; C000608732:murrafoline-E; C000608731:murrastifoline-C; C443728:murrayafoline A; C000601876:murrayamine D; D010165:Palladium
keywords: C−H bond activation; alkaloids; copper; cyclisation; natural products; palladium