Bronsted acid-catalyzed highly stereoselective arene-ynamide cyclizations.: A novel keteniminium Pictet-Spengler cyclization syntheses of (±)-desbromoarborescidines A and C

A Bronsted acid-catalyzed highly stereoselective arene-ynamide cyclization is described. These reactions constitute a keteniminium variant of Pictet-Spengler cyclizations, leading to efficient synthesis of nitrogen heterocycles and related alkaloids. Total syntheses of desbromoarborescidines A and C are illustrated here as first applications of this methodology.