title: Total Synthesis of (±)-Berkeleyone A.
abstract: A 13-step total synthesis of the fungal meroterpenoid berkeleyone A is reported. The molecular skeleton is formed using the first examples of two critical construction reactions: (1) an epoxide-initiated, β-ketoester-terminated polycyclization, and (2) an isomerization-cyclization cascade to generate the remaining bicyclo[3.3.1]nonane framework. The resulting 6-step synthesis of the carbocyclic core of the berkeleyone natural products has been used to access protoaustinoid A and berkeleyone A, and will aid future biosynthetic investigations into the origin of related natural products.
authors.affiliation: Department of Chemistry, Yale University , 275 Prospect Street, New Haven, Connecticut 06520-8107, United States.
authors.forename: Masha
authors.initials: M
authors.lastname: Elkin
authors.affiliation: Department of Chemistry, Yale University , 275 Prospect Street, New Haven, Connecticut 06520-8107, United States.
authors.forename: Suzanne M
authors.initials: SM
authors.lastname: Szewczyk
authors.affiliation: Department of Chemistry, Yale University , 275 Prospect Street, New Haven, Connecticut 06520-8107, United States.
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Scruse
authors.affiliation: Department of Chemistry, Yale University , 275 Prospect Street, New Haven, Connecticut 06520-8107, United States.
authors.forename: Timothy R
authors.identifier: 0000-0001-8741-7236
authors.initials: TR
authors.lastname: Newhouse
mesh_terms: D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D018942:Macrolides; D013729:Terpenes; C493366:berkeleydione; C493367:berkeleytrione