title: Rapid synthesis of the N-methylwelwitindolinone skeleton.
abstract: An efficient, convergent synthesis of the core bicyclo[4.3.1]decane ring system of welwitindolinones is described. Key steps in the synthesis include an intramolecular palladium-catalyzed enolate arylation reaction to create the desired bicyclic skeleton and a Curtius rearrangement to install the bridgehead isocyanate unit. [reaction: see text]
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, USA.
authors.forename: James A
authors.initials: JA
authors.lastname: MacKay
authors.forename: Raynauld L
authors.initials: RL
authors.lastname: Bishop
authors.forename: Viresh H
authors.initials: VH
authors.lastname: Rawal
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D000458:Cyanobacteria / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry
chemical_list: D000470:Alkaloids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D026121:Indole Alkaloids; C092268:N-methylwelwitindolinone C isothiocyanate; D010165:Palladium