Rhodium(III)-Catalyzed Asymmetric C–H Activation of <i>N</i>-Methoxybenzamide with Quinone and Its Application in the Asymmetric Synthesis of a Dihydrolycoricidine Analogue
Xiaoqiang Yan, Peng Zhao, Hao Liang, Hui Xie, Ji‐Jun Jiang, Shaohua Gou, Jun Wang
Abstract
A chiral CpRhIII-catalyzed asymmetric C–H activation reaction of N-methoxybenzamides with quinones has been developed to efficiently forge chiral tricyclic hydrophenanthridinone scaffolds in ≤88% yield and ≤94% ee. With this methodology as the key step, an enantioenriched dihydrolycoricidine derivative has been synthesized in 64% overall yield in five steps.
Topics & Concepts
ChemistryCatalysisRhodiumQuinoneStereochemistryEnantioselective synthesisCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsChemical synthesis and alkaloidsAlkaloids: synthesis and pharmacology