This research program focuses on the discovery and development of synthetic methods suitable for the synthesis of complex molecular architectures. Five specific structures embracing unusual structural motifs are targeted. Cyclization of homoallylic triflates will be exploited in the synthesis of polycyclopropane-containing structures of the type found in the unusual antifungal agent FR900848. Coupled intramolecular [2+2] photoaddition/retro-Mannich fragmentation reactions will produce spiroamines, including the spiro[6.5]imine forming the core of the pinnatoxins. A new approach to the hydrindane nucleus through cationic cyclization of ene diynes will be explored, leading to the fused tetracycle representing the core unit of the marine metabolite neomangicol A. Synthesis of the unique sesquiterpene ligulaverin A will test a biogenetic hypothesis involving an unprecedented intramolecular Diels-Alder reaction. Synthesis of elisabethane-type diterpenoids will be approached through sequential asymmetric Doetz and intramolecular Diels-Alder reactions.
With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor James D. White, of the Department of Chemistry at Oregon State University. Professor White will focus his work on the synthesis of complex organic molecules through novel adaptation and coupling of various molecular transformations. These studies will develop the tools required for the synthesis of the complex molecules displaying interesting and important biological and biochemical activity and will serve as a training ground for the next generation of synthetic chemists required to prepare such molecules.
