Modular Total Syntheses of Hyperforin, Papuaforins A, B, and C via Gold(I)-Catalyzed Carbocyclization.

ABSTRACT

The remarkable biological activities of polyprenylated polycyclic acylphloroglucinols (PPAPs) combined with their highly oxygenated and densely functionalized frameworks have stimulated the interest of synthetic organic chemists over the past decade. Herein, we report the concise total syntheses of four natural products PPAPs, of which some have antibacterial properties, notably hyperforin and papuaforin A. The salient features of this strategy are the short and gram-scalable synthesis of densely substituted PPAPs scaffolds via a Au(I)-catalyzed carbocyclization and the late-stage functionalization for a unified access to a wide variety of PPAPs.