Total syntheses of hyperforin and papuaforins A-C, and formal synthesis of nemorosone through a gold(I)-catalyzed carbocyclization.
The remarkable biological activities of polyprenylated polycyclic acylphloroglucinols (PPAPs) combined with their highly decorated bicyclo[3.3.1]nonane-2,4,9-trione frameworks have inspired synthetic organic chemists over the last decade. The concise total syntheses of four natural products PPAPs; hyperforin and papuaforins A-C, and the formal synthesis of nemorosone are reported. Key to the realization of this strategy is the short and scalable synthesis of densely substituted PPAP scaffolds through a gold(I)-catalyzed 6-endo-dig carbocyclization of cyclic enol ethers for late-stage functionalization.
Centre for Catalysis, Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, On, K1N 6N5 (Canada).
Gabriel
G
Bellavance
Louis
L
Barriault
D001577:Benzophenones / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry*
D001577:Benzophenones; D001688:Biological Products; D013729:Terpenes; C437463:nemorosone; C000597349:papuaforin A; C000597351:papuaforin B; C000597353:papuaforin C; D006046:Gold; D010696:Phloroglucinol; C001654:hyperforin
PPAPs; gold; homogeneous catalysis; natural products; total synthesis