Regioselective Synthesis of Substituted Carbazoles, Bicarbazoles, and Clausine C
Gary L. Points, Christopher M. Beaudry
Abstract
Substituted carbazoles are efficiently constructed from 3-triflato-2-pyrones and alkynyl anilines. Multiple substituents are tolerated on the carbazole, and complete control of regiochemistry is observed. Complicated and sterically congested substitution patterns are produced. This strategy is also used to prepare substituted bicarbazoles and related biaryls. Finally, the method was showcased in a synthesis of the carbazole natural product clausine C.
Topics & Concepts
RegioselectivityCarbazoleChemistrySteric effectsNatural productCombinatorial chemistryStereochemistryOrganic chemistryCatalysisAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsChemical synthesis and alkaloids