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Total Syntheses of Hyperforin and Papuaforins A–C, and Formal Synthesis of Nemorosone through a Gold(I)‐Catalyzed Carbocyclization
Author(s) -
Bellavance Gabriel,
Barriault Louis
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201403939
Subject(s) - hyperforin , total synthesis , chemistry , catalysis , nonane , combinatorial chemistry , enol , formal synthesis , stereochemistry , organic chemistry , nanotechnology , materials science , biology , hypericum perforatum , pharmacology
Abstract 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.