Bridgehead arylation: a direct route to advanced intermediates for the synthesis of C-20 diterpene alkaloids.
[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.
Williams
Craig M
CM
Chemistry Department, School of Molecular and Microbial Sciences, University of Queensland, St. Lucia, 4072, Queensland, Australia. c.williams3@mailboz.uq.edu.au
Mander
Lewis N
LN
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
D000470:Alkaloids; D001372:Aza Compounds; D001952:Bridged-Ring Compounds; D001965:Bromides; D004224:Diterpenes; D011083:Polycyclic Compounds; C111428:kobusine; D012834:Silver; D010165:Palladium