title: Bridgehead arylation: a direct route to advanced intermediates for the synthesis of C-20 diterpene alkaloids.
abstract: [reaction: see text] Rapid access to the ABCE ring system of the C(20) diterpene alkaloids was achieved by silver(I)-promoted intramolecular Friedel-Crafts arylation of a functional group-specific 5-bromo-3-azabicyclo[3.3.1]nonane derivative.
authors.affiliation: Chemistry Department, School of Molecular and Microbial Sciences, University of Queensland, St. Lucia, 4072, Queensland, Australia. c.williams3@mailboz.uq.edu.au
authors.forename: Craig M
authors.initials: CM
authors.lastname: Williams
authors.forename: Lewis N
authors.initials: LN
authors.lastname: Mander
mesh_terms: D000215:Acylation; D000470:Alkaloids / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001372:Aza Compounds; D001952:Bridged-Ring Compounds; D001965:Bromides; D004224:Diterpenes; D011083:Polycyclic Compounds; C111428:kobusine; D012834:Silver; D010165:Palladium