title: Total Synthesis of Hyperforin.
abstract: A 10-step total synthesis of the polycyclic polyprenylated acylphloroglucinol (PPAP) natural product hyperforin from 2-methylcyclopent-2-en-1-one is reported. This route was enabled by a diketene annulation reaction and an oxidative ring expansion strategy designed to complement the presumed biosynthesis of this complex meroterpene. The described work enables the preparation of a highly substituted bicyclo[3.3.1]nonane-1,3,5-trione motif in only six steps and thus serves as a platform for the construction of easily synthesized, highly diverse PPAPs modifiable at every position.
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Chi P
authors.initials: CP
authors.lastname: Ting
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Maimone
mesh_terms: D060326:Chemistry Techniques, Synthetic; D010084:Oxidation-Reduction; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013729:Terpenes; D010696:Phloroglucinol; C001654:hyperforin