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

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 PPAP

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

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 PPAP

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

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 PPAP

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

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 PPAP

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

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 PPAP

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

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 PPAP

Total Syntheses of Disorazoles A₁ and B₁ and Full Structural Elucidation of Disorazole B₁

Described herein are the first total syntheses of naturally occurring antitumor agents disorazoles A₁ and B₁ and the full structural assignment of the latter. The syntheses were achieved through convergent strategies employing enantioselective constructions of the required building blocks, including a novel Sharpless epoxidation/enzymatic kinetic resolution of stannane-containing substrates that led selectively to both enantiomeric forms of an epoxy vinyl stannane, and a series of coupling reactions, including a Wittig reaction, a Suzuki coupling, a Stille coupling, a Yamaguchi esterification and a Yamaguchi macrolactonization