SYNTHESIS OF NOVEL MARINE MACROLIDES

University Of Iowa, Iowa City IA

Investigators

Abstract

Professor Horacio F. Olivo, of the Medicinal Natural Products Chemistry Department at the University of Iowa, is supported by the Organic and Macromolecular Chemistry Program for his studies of the synthesis of novel marine macrolides. Professor Olivo is exploring the efficacy of the Ireland-Claisen rearrangement of products derived from biocatalytic desymmetrization of cyclopentenediesters to prepare substituted bicyclic lactones. Mild methods for the generation of enynes via palladium-catalyzed coupling of 1,1-dihalo-1-alkenes with vinylstannanes and the chemoselectivity of bis-haloalkenes in Ni/Cr coupling reactions are also being examined. Newly developed methodologies are applied to the synthesis of callipeltoside-A and auriside-A. Much current effort in the field of organic synthesis is directed toward the selective preparation of molecules with precisely defined three-dimensional structures. Biological catalysis is an attractive approach, given its potentially low cost and minimal environmental impacts. By developing new methodologies for the conversion of products of biocatalysis to useful organic molecules, Professor Horacio F. Olivo, of the Medicinal Natural Products Chemistry Department at the University of Iowa, is demonstrating biocatalysis as an efficient and low-cost method for the generation of valuable intermediates in organic synthesis. With the support of the Organic and Macromolecular Chemistry Program, Professor Olivo is exploring general synthetic methodology utilizing products of biological catalysis and applying this methodology to the synthesis of several complex natural products of marine origin.