Rhodium(III)-Catalyzed Asymmetric C-H Activation of N-Methoxybenzamide with Quinone and Its Application in the Asymmetric Synthesis of a Dihydrolycoricidine Analogue

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.