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Enantioselective Syntheses of Heteroyohimbine Natural Products: A Unified Approach through Cooperative Catalysis
Author(s) -
Younai Ashkaan,
Zeng BiShun,
Meltzer Herbert Y.,
Scheidt Karl A.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502011
Subject(s) - enantioselective synthesis , stereocenter , enamine , chemistry , catalysis , organocatalysis , combinatorial chemistry , organic chemistry , stereochemistry
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.