New fragmentation reactions and strategies for chemical synthesis

Florida State University, Tallahassee FL

Investigators

Abstract

This project focuses on the development and application of carbon carbon bond cleavage reactions for the synthesis of complex molecular structures. While much effort in organic synthesis is pointed toward making new bonds, the ability to break specific bonds as needed can greatly simplify synthetic challenges. The proposed reactions of heterocyclic vinylogous acyl triflates (VATs) create a unique, general strategy for the synthesis of acyl-protected homopropargyl alcohols and amines, which can be difficult to prepare by other means. The proposed total synthesis of palmerolide A takes advantage of the chiral homopropargyl alcohols that can be made available by this methodology. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Gregory B. Dudley of the Department of Chemistry and Biochemistry at Florida State University. Professor Dudley's research efforts revolve around the development of new strategies for organic synthesis, with an emphasis on bond-cleaving fragmentation methods. Successful development of the methodology will impact chemical synthesis, especially as it pertains to the pharmaceutical industry.