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Published on: January 19, 2016
Concise Total Synthesis of Dioncophylline E through an ortho-Arylation Strategy
Hamish D Toop1, Jason S Brusnahan2, Jonathan C Morris1
1School of Chemistry, UNSW, Sydney, NSW, 2052, Australia.
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.
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