Application of Cascade Processes for the Synthesis of Polycyclic Ring Systems

Emory University, Atlanta GA

Investigators

Abstract

The foci of this research are three-fold. First , a novel [4+2]-cycloaddition -rearrangement sequence will be used to set the ABCE cyclic core of the aspidosperma alkaloid skeleton. Second, a tandem thionium/N-acyliminium ion cyclization strategy will be used to afford the pyrrolo[2,3-d]carbazole ring framework found in deethylibophyllidene. Third, the transition metal mediated cyclization of acetylenic diazoketoamides will be studied as a route to the synthesis of a number of alkaloids including strychnine. With this Renewal award, the Organic and Macromolecular Chemistry Program is supporting the research efforts of Dr. Albert Padwa of the Department of Chemistry at Emory University. Professor Padwa will focus his work on the development of tandem, or cascade, methods for the formation of several carbon-carbon bonds and/or rings systems in a single operation. Using combinations of cationic, anionic, radical, carbenoid or pericyclic processes will lead to the preparation of structurally diverse synthetic targets possessing interesting biological properties. The research has broader impact for the training of graduate students and for the development of methodology pertinent to the pharmaceutical industry.