Preparation of enamide skeletons via Rh(I)-catalyzed Alder-ene reaction

ORGN 948

Kay M. Brummond, kbrummon@pitt.edu, Center for Chemical Methodologies and Library Development, Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 and Bingli Yan, biy4@pitt.edu, Department of Chemistry, University of Pittsburgh, 815 Chevron Science Center, 219 Parkman Ave., Pittsburgh, PA 15260.
Diversity Oriented Synthesis (DOS) constitutes a powerful new strategy for the synthesis of small molecules that are predicted to have important biological activity. Our DOS approach is based on the use of a pivotal substrate that when subjected to different reaction conditions, affords new, skeletally unique products. In this presentation, we will discuss the synthesis of novel conjugated triene ring systems. Using [Rh(CO)2Cl)2 as the catalyst under nitrogen atmosphere [5, 5], [5, 6] and [5, 7] bicyclic skeletons are afforded in good yields. The scope and limitations of this triene forming method to prepare enamides will be discussed along with the potential application of this strategy to the total synthesis of natural products.