Abstract:

The presentation will detail the development of a synthetic route to pleuromutilin, a structurally complex antibacterial diterpenoid natural product. The evolution of our strategy was defined by the unique chemistry of the mutilin tricyclic scaffold, and relied on an oxidative ring-expansion of a tetracyclic precursor that was assembled by a cycloaddition-radical cyclization approach. The completed synthesis is the shortest reported to date and proceeded with complete stereochemical relay throughout the sequence.