Enone-Initiated Nickel-Catalyzed Carbocyclizations

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The focus of the research effort is the use of enone-initiated, nickel-catalyzed carbocyclization reactions to afford highly functionalized, complex products from simple, readily available substrates. The methodology will be applied to the synthesis of the cis-fused (3.2.0) bicyclooctane framework of caracyclin, the tricyclic ring skeleton of pentalenic acid and the exocyclic, trisubstituted alkenes of geissoschizine and Z-isositsirikine. The educational plan includes outreach efforts to Detroit schools, the introduction of molecular modeling and on-line searching to undergraduate courses, course development at the graduate level and collaborative graduate training with top scientists at Parke-Davis. With this CAREER award, the Synthetic Organic Program is supporting the research and educational activities of Dr. John Montgomery of the Department of Chemistry at Wayne State University. Professor Montgomery will focus his research efforts on drawing together nickel- promoted conjugate additions with meta-mediated cyclizations as the basis for a new cyclization protocol that will result in the construction of the complex ring systems that occur in natural products. The educational plan includes innovative teaching approaches in chemistry at the high school, undergraduate and graduate levels.