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

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.

• Authors: Ashkaan Younai, Bi-Shun Zeng, Herbert Y Meltzer, Karl A Scheidt
• Journal: Angewandte Chemie (International ed. in English) (Angew Chem Int Ed Engl) Vol. 54 Issue 23 Pg. 6900-4 (Jun 01 2015) ISSN: 1521-3773 [Electronic] Germany
• PMID: 25914164 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemical References

• Amines
• Biological Products
• Yohimbine

Topics

• Amines (chemistry)
• Biological Products (chemical synthesis, chemistry)
• Catalysis
• Crystallography, X-Ray
• Hydrogen Bonding
• Models, Molecular
• Molecular Structure
• Stereoisomerism
• Yohimbine (chemical synthesis, chemistry)