A new beta-carbolinone synthesis using a Rh(II)-promoted [3 + 2]-cycloaddition and Pd(0) cross-coupling/Heck cyclization chemistry.
[reaction: see text]. A short and efficient synthesis of the beta-carbolinone ring system was achieved using a rhodium(II)-catalyzed [3 + 2]-cycloaddition, a Pd(0)-catalyzed C-N amination reaction, and a subsequent intramolecular Heck reaction as the key synthetic steps.
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Joel M
JM
Harris
Albert
A
Padwa
D000586:Amination; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*
D002243:Carbolines; D006575:Heterocyclic Compounds, 3-Ring; D006576:Heterocyclic Compounds, 4 or More Rings; D010165:Palladium; D012428:Ruthenium