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Gram-Scale Total Synthesis of (±)-Ibogamine
Alexander J Hughes1, Steven D Townsend1
1Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States.
Abstract:
We describe the gram-scale total synthesis of (±)-ibogamine in nine steps and 24% overall yield. The approach features a Mitsunobu fragment coupling and macrocyclic Friedel-Crafts alkylation to establish the nitrogen-containing core of ibogamine. A regio- and diastereoselective hydroboration allows for simultaneous formation of the tetrahydroazepine and isoquinuclidine ring systems via sulfonamide deprotection and concomitant intramolecular cyclization.
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