title: Adventures in bridgehead substitution chemistry: synthesis of polycyclic polyprenylated acylphloroglucinols (PPAPs).
abstract: The polycyclic polyprenylated acylphloroglucinol (PPAP) family of natural products includes important compounds with notable biological activities, such as garsubellin A, hyperforin and clusianone. The synthesis of these complex, bridged, highly oxidized and substituted systems presents a formidable challenge to synthetic chemists. This feature article describes how the use of unconventional bridgehead substitution chemistry has enabled the synthesis of these natural products and their analogues.
authors.affiliation: School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, UK. n.simpkins@bham.ac.uk
authors.forename: Nigel S
authors.initials: NS
authors.lastname: Simpkins
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001577:Benzophenones / Q000138:chemical synthesis / Q000494:pharmacology; D016227:Benzoquinones; D001688:Biological Products / Q000138:chemical synthesis* / Q000494:pharmacology; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D002392:Catechin / Q000737:chemistry; D045744:Cell Line, Tumor; D006801:Humans; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D013729:Terpenes / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: C118110:7-epiclusianone; D000970:Antineoplastic Agents; D001577:Benzophenones; D016227:Benzoquinones; D001688:Biological Products; D001643:Bridged Bicyclo Compounds; D013729:Terpenes; C106690:garsubellin A; C437463:nemorosone; D002392:Catechin; D010696:Phloroglucinol