Three-step synthesis of an annulated β-carboline via palladium catalysis.

ABSTRACT: The synthesis of β-carbolines is a mature field, yet new methods are desirable to introduce new functionality onto the core scaffold. We describe the incorporation of an additional fused ring onto the β-carboline via a novel palladium-catalyzed, one-pot Sonogashira coupling/intramolecular [2+2+2] cyclization. This method generates three rings in one flask and produces an annulated β-carboline in 80% yield. A preliminary mechanistic study into the sequence of events is described, which confirms an unprecedented catalytic role for palladium.

SUBMITTER: Mulcahy SP 

PROVIDER: S-EPMC3861870 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature