Rapid synthesis of the N-methylwelwitindolinone skeleton.
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]
MacKay
James A
JA
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, USA.
Bishop
Raynauld L
RL
Rawal
Viresh H
VH
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
D000470:Alkaloids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D026121:Indole Alkaloids; C092268:N-methylwelwitindolinone C isothiocyanate; D010165:Palladium