Concise Total Synthesis of Dioncophylline E through an ortho‐Arylation Strategy. Issue 29 (4th May 2017)

• Record Type: Journal Article
• Authors: Toop, Hamish D.; Brusnahan, Jason S.; Morris, Jonathan C.
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 29(2017)
• Page Start: 8536
• Page End: 8538
• Publication Date: 2017-05-04
• Subjects: alkaloids -- aryllead triacetate -- biaryls -- dioncophylline E -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201701136
• Languages: English
• ISSNs: 1433-7851

Abstract

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.