Three-component coupling via the squarate ester cascade as a concise route to the bioactive triquinane sesquiterpene hypnophilin.
[reaction: see text] A squarate ester cascade is used to provide in one step, via the coupling of three reactants, a highly oxygenated linear triquinane product. The latter is transformed in nine steps into hypnophilin. The access route involves a combination of chlorination, reduction, dehydration, and oxidation maneuvers in the proper sequence.
Geng
Feng
F
Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA.
Liu
Jian
J
Paquette
Leo A
LA
D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000138:chemical synthesis*
D012717:Sesquiterpenes; C446680:hypnophilin