Enantioselective syntheses of heteroyohimbine natural products: A unified approach through cooperative catalysis

Ashkaan Younai, Bi Shun Zeng, Herbert Y. Meltzer, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

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. The enantioselective total syntheses of the natural products alstonine and serpentine are presented. They proceed through a sequence with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step.

Original languageEnglish (US)
Pages (from-to)6900-6904
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number23
DOIs
StatePublished - Jun 1 2015

Keywords

  • cooperative catalysis
  • enamine catalysis
  • enantioselectivity
  • schizophrenia
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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