Total synthesis of Sorbicillactone A: inspiration for catalyst and methodology development

Abstract

The unique reactivity and usefulness of cyclohexadienones has been the central focus of my graduate research. Our group has a particular interest in the synthesis and methodology of this structural motif because it can be used as a synthetic building block for the construction of complex molecules, specifically, natural products. We were inspired to design a synthetic route to sorbicillactone A, a bioactive marine natural product, using a cyclohexadienone as the key building block. Chapter 1 will give a more detailed background on cyclohexadienones: how they are synthesized and how they have been utilized in natural product synthesis. Sorbicillactone A is part of a larger family of natural products called sorbicillinoids, therefore, Chapter 2 is based on a review that we wrote summarizing the various sorbicillinoid compounds that have been isolated, the biosynthetic proposals that have been put forth, and the various synthetic efforts that have already been carried out. Chapter 3 will cover our own synthetic efforts on the total synthesis of sorbicillactone A and a related epimer. Curious diastereoselectivity was encountered during these efforts that was further explored and will be discussed in Chapter 4. Finally, Chapter 5 will highlight our endeavors in designing chiral aryl iodide catalysts for the asymmetric synthesis of cyclohexadienones.