Reports: AC1 45568-AC1: Synthesis of Complex Indoles and Related Natural Products

Gordon W. Gribble, Dartmouth College

In our final year of support we have been able to synthesize tetracyclic gamma-carbolines via the nucleophilic addition of lithiated heterocycles to 3-nitroindoles, followed by reductive aminationof the nitro group and a Bischer-Napieralski cyclization.  This work was published in a special issue of Heterocycles dedicated to Professor Akira Suzuki who this week won the Nobel Prize in Chemistry (shared).  Another finished project is the addition of cuprate nucleophiles to 1,2-bis(phenylsulfonyl)indole to afford 3-substituted indoles.  This was published this year in Arkivoc in a special issue dedicated to Professor James Cook.  Finally, we have just submitted our chemistry involving the 1,3-dipolar cycloaddition of munchnones to nitro-styrenes to Heterocycles in a special issue devoted to Professor Albert Eschenmosher.  All of this work was supported by the Petroleum Research Fund.

 
Moving Mountains; Dr. Surpless
Desert Sea Fossils; Dr. Olszewski
Lighting Up Metals; Dr. Assefa
Ecological Polymers; Dr. Miller