Concise Total Synthesis of Dioncophylline E through an ortho‐Arylation Strategy. Issue 29 (4th May 2017) - Toop, Hamish D.
Abstract: The 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. Abstract : Access granted : Total synthesis of the potent antimalarial 7, 3′‐linked naphthylisoquinoline alkaloid dioncophylline E was achieved. The synthesis proceeds in 12 steps (longest linear sequence) and 15 % overall yield. Key transformations include an ortho ‐arylation of a naphthol with an aryllead triacetate to give the sterically hindered biaryl bond, and a three‐step sequence to stereoselectively generate the trans ‐1, 3‐dimethyl‐1, 2, 3, 4‐tetrahydroisoquinoline moiety.