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Enantioselective Syntheses of Heteroyohimbine Natural Products: A Unified Approach through Cooperative Catalysis |
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| Authors: | Ashkaan Younai Bi‐Shun Zeng Herbert Y Meltzer Karl A Scheidt |
| Institution: | 1. Department of Chemistry Center for Molecular Innovation and Drug Discovery, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA);2. Departments of Psychiatry and Behavioral Sciences, Physiology, Feinberg School of Medicine, Northwestern University, 303 E Chicago Avenue, Chicago, IL 60611 (USA) |
| Abstract: | Alstonine and serpentine are pentacyclic indoloquinolizidine alkaloids (referred to as “anhydronium bases”) containing three contiguous stereocenters. Each possesses interesting biological activity, with alstonine being the major component of a plant‐based remedy to treat psychosis and other nervous system disorders. This work describes the enantioselective total syntheses of these natural products with a cooperative hydrogen bonding/enamine‐catalyzed Michael addition as the key step. |
| Keywords: | cooperative catalysis enamine catalysis enantioselectivity schizophrenia total synthesis |