Concise Total Synthesis of Dioncophylline E through an ortho‐Arylation Strategy

Abstract

AbstractThe first total synthesis of the potent antimalarial 7,3′‐linked naphthylisoquinoline alkaloid dioncophylline E (1) has been completed. The synthesis proceeds in 12 steps (longest linear sequence) and in 15 % overall yield. Key transformations include an ortho‐arylation of a naphthol with an aryllead triacetate to construct the sterically hindered biaryl bond, and a three‐step sequence to stereoselectively generate the trans‐1,3‐dimethyl‐1,2,3,4‐tetrahydroisoquinoline moiety.