title: Total Synthesis of (-)-Nemorosone and (+)-Secohyperforin.
abstract: A general strategy for the synthesis of polycyclic polyprenylated acylphloroglucinols is described in which a scalable, Lewis acid catalyzed epoxide-opening cascade cyclization is used to furnish common intermediate 4. The utility of this approach is exemplified by the total syntheses of both ent-nemorosone and (+)-secohyperforin, which were each accomplished in four steps from this intermediate.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02139, United States.
authors.forename: Brian A
authors.initials: BA
authors.lastname: Sparling
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02139, United States.
authors.forename: James K
authors.initials: JK
authors.lastname: Tucker
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02139, United States.
authors.forename: David C
authors.initials: DC
authors.lastname: Moebius
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02139, United States.
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Shair
mesh_terms: D001577:Benzophenones / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; 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: D001577:Benzophenones; D004852:Epoxy Compounds; D058116:Lewis Acids; D013729:Terpenes; C437463:nemorosone; C525824:secohyperforin; D010696:Phloroglucinol