N-Heterocyclic carbene-catalyzed annulation of cyclic β-enamino esters with enals: access to functionalized indolo[2,3-a]quinolizidines

Org Biomol Chem. 2015 Apr 28;13(16):4661-7. doi: 10.1039/c5ob00176e.

Abstract

A novel synthetic approach to functionalized indolo[2,3-a]quinolizidines is developed via an N-heterocyclic carbene (NHC)-catalyzed annulation of cyclic β-enamino esters with enals . This methodology offers a pathway for quick and efficient construction of an indolo[2,3-a]quinolizidine skeleton which is a core structure of many natural products with diverse bioactivities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Carbon / chemistry
  • Catalysis
  • Chemistry, Pharmaceutical
  • Chromatography, Thin Layer
  • Esters / chemistry*
  • Heterocyclic Compounds / chemistry
  • Indoles / chemistry
  • Light
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Quinolizidines / chemistry
  • Solvents / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Esters
  • Heterocyclic Compounds
  • Indoles
  • Quinolizidines
  • Solvents
  • carbene
  • Carbon
  • Methane