title: Total synthesis of the biscarbazole alkaloids murrafoline A-D by a domino sonogashira coupling/claisen rearrangement/electrocyclization reaction.
abstract: Why take things one step at a time? Aryl-pyran-linked biscarbazole alkaloids of the murrafoline group (see crystal structure of murrafoline A; dark gray: C, red: O, blue: N) were accessed readily by a novel domino reaction sequence involving Sonogashira coupling, a Claisen rearrangement, and electrocyclization. The one-pot procedure enables the straightforward synthesis of these structurally challenging alkaloids in only a few steps.
authors.affiliation: Department of Chemistry, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden (Germany) http://www.chm.tu-dresden.de/oc2/
authors.forename: V Pavan
authors.initials: VP
authors.lastname: Kumar
authors.forename: Konstanze K
authors.initials: KK
authors.lastname: Gruner
authors.forename: Olga
authors.initials: O
authors.lastname: Kataeva
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; D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D002227:Carbazoles
keywords: CH bond activation; X-ray diffraction; alkaloids; natural products; palladium