An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y

Abstract

A novel synthetic methodology has been developed for the synthesis of dihydro-β-carboline derivatives employing oxidative amidation–Bischler–Napieralski reaction conditions using tryptamine and 2,2-dibromo-1-phenylethanone as key starting materials. A number of dihydro-β-carboline derivatives have been synthesized in moderate to good yields using this methodology. Attempts were made towards the conversion of these dihydro-β-carbolines to naturally occurring eudistomin alkaloids.

Keywords

• Bischler–Napieralski reaction
• dihydro-β-carboline derivatives
• dihydro-eudistomin
• eudistomin
• keto amide
• oxidative amidation