Enantioselective Syntheses of Heteroyohimbine Natural Products: A Unified Approach through Cooperative Catalysis

Ashkaan Younai; Bi-Shun Zeng; Herbert Y Meltzer; Karl A Scheidt

doi:10.1002/anie.201502011

Enantioselective Syntheses of Heteroyohimbine Natural Products: A Unified Approach through Cooperative Catalysis

Angew Chem Int Ed Engl. 2015 Jun 1;54(23):6900-4. doi: 10.1002/anie.201502011. Epub 2015 Apr 27.

Authors

Ashkaan Younai¹, Bi-Shun Zeng¹, Herbert Y Meltzer², Karl A Scheidt³

Affiliations

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).
³ Department of Chemistry Center for Molecular Innovation and Drug Discovery, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA). scheidt@northwestern.edu.

PMID: 25914164
DOI: 10.1002/anie.201502011

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines / chemistry*
Biological Products / chemical synthesis*
Biological Products / chemistry
Catalysis
Crystallography, X-Ray
Hydrogen Bonding
Models, Molecular
Molecular Structure
Stereoisomerism
Yohimbine / chemical synthesis*
Yohimbine / chemistry

Substances

Amines
Biological Products
Yohimbine