Co(III)-Catalyzed Annulative Vinylene Transfer via C–H Activation: Three-Step Total Synthesis of 8-Oxopseudopalmatine and Oxopalmatine
Xinghua Li, Ting Huang, Ying Song, Yue Qi, Limin Li, Yanping Li, Qi Xiao, Yuanfei Zhang
Abstract
The Co(III)-catalyzed redox-neutral annulation of benzamides and acrylamides with vinylene carbonate for the synthesis of isoquinolinones and pyridinones has been developed. This protocol employing inexpensive Co(III) as the catalyst tolerated diverse functional groups and substitution patterns, affording the target products with good to excellent yields. The synthetic utility of this transformation was demonstrated by a three-step synthesis of gusanlung D, 8-oxopseudopalmatine, and oxopalmatine.
Topics & Concepts
ChemistryAnnulationCatalysisCombinatorial chemistryTransformation (genetics)Organic chemistryGeneBiochemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms