Nitrovinylindoles as Heterotrienes: Electrocyclic Cyclization En Route to β-Carbolines: Total Synthesis of Alkaloids Norharmane, Harmane, and Eudistomin N

Org Lett. 2022 Oct 7;24(39):7062-7066. doi: 10.1021/acs.orglett.2c02483. Epub 2022 Sep 27.

Abstract

Unusual cascade transformation was developed involving microwave assisted electrocyclic cyclization of aci (alkylideneazinic acid) forms of nitrovinylindoles acting as heterotrienes. Subsequent one-pot reduction allowed for efficient access to β-carbolines, including several natural products, alkaloids norharmane, harmane and eudistomin N.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids*
  • Biological Products*
  • Carbolines
  • Cyclization
  • Harmine / analogs & derivatives

Substances

  • Alkaloids
  • Biological Products
  • Carbolines
  • Harmine
  • eudistomin N
  • harman
  • norharman