Liam Landon Rose Hills
Synthesis of Dalesconol A using Acenaphthene Bis-Tosyl Hydrazones
The fungi-derived natural product dalesconol A is a biologically active and structurally intriguing polyketide. These qualities make an efficient, novel synthesis of dalesconol A incredibly useful, not only by enabling further investigation of its immunosuppressive activity, but by advancing the field of synthetic chemistry through the discovery of new strategies to access this challenging structure. The synthetic route outlined herein will explore the capabilities of tosylhydrazones as coupling partners in metal-catalyzed cascade reactions. Previous research regarding the use of tosylhydrazones in catalysis demonstrated their effectiveness in Pd-catalyzed coupling reactions, but the extent of this reactivity is underexplored. Contrary to traditional coupling partners, tosylhydrazones enable the formation of multiple new C-C bonds, which enables a concise total synthesis. This project centers around the further exploration and expansion of tosylhydrazones in catalysis through the synthesis of dalesconol A. In the future, these findings may enable a strategy for the concise synthesis of other natural products, including those with similar structural challenges as dalesconol A.