Organoiron Complexes in Organic Synthesis

Case Western Reserve University, Cleveland OH

Investigators

Abstract

This project will continue research on the development and applications of new reactions involving organoiron complexes discovered in the Principal Investigator's laboratory. Specifically, the scope of cyclocoupling reactions between a diene complexed with an iron tricarbonyl group and an alkene, the formal [6+2] ene reactions, will be studied. This reaction type is unique to iron tricarbonyl complexes and requires the stoichiometric use of the organometallic group to prevent competing intramolecular Diels-Alder reactions. The application of an asymmetric double version of this ene reaction, carried out in a tandem manner, will be explored as an approach to the chemical synthesis of 18-deoxycytochalasin H, which is of interest as an HIV protease inhibitor. A variant of this [6+2] ene reaction in which the pendant alkene is replaced by aldehyde and imine functionality, which broadens the scope of the process, will also be studied. Application of tandem alkene/aldehyde [6+2] ene reactions to the chemical synthesis of magellaninone, a structurally complex lycopodium alkaloid natural product, will be pursued as a long term future goal. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Anthony J. Pearson of the Department of Chemistry at Case Western Reserve University. Professor Pearson's research efforts revolve around the development of metal-mediated reactions for the formation of C-C bonds. Such chemistry will contribute to environmentally benign methods for chemical synthesis as the readily available iron is used as the active metal that mediates the key reactions. Successful development of the methodology will have an impact on synthesis in the pharmaceutical and agricultural industries.