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

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.