Enantioselective Syntheses of Heteroyohimbine Natural Products: A Unified Approach through Cooperative Catalysis.
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.
Department of Chemistry Center for Molecular Innovation and Drug Discovery, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA).
Ashkaan
A
Younai
Department of Chemistry Center for Molecular Innovation and Drug Discovery, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA).
Bi-Shun
BS
Zeng
Departments of Psychiatry and Behavioral Sciences, Physiology, Feinberg School of Medicine, Northwestern University, 303 E Chicago Avenue, Chicago, IL 60611 (USA).
Herbert Y
HY
Meltzer
Department of Chemistry Center for Molecular Innovation and Drug Discovery, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA). scheidt@northwestern.edu.
Karl A
KA
Scheidt
D000588:Amines / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D015016:Yohimbine / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D001688:Biological Products; D015016:Yohimbine
cooperative catalysis; enamine catalysis; enantioselectivity; schizophrenia; total synthesis