title: Enantioselective total synthesis of hyperforin.
abstract: A modular, 18-step total synthesis of hyperforin is described. The natural product was quickly accessed using latent symmetry elements, whereby a group-selective, Lewis acid-catalyzed epoxide-opening cascade cyclization was used to furnish the bicyclo[3.3.1]nonane core and set two key quaternary stereocenters.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
authors.forename: Brian A
authors.initials: BA
authors.lastname: Sparling
authors.forename: David C
authors.initials: DC
authors.lastname: Moebius
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Shair
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D003500:Cyclization; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001643:Bridged Bicyclo Compounds; D058116:Lewis Acids; D013729:Terpenes; D010696:Phloroglucinol; C001654:hyperforin