Aza-Prins-pinacol approach to 7-azabicyclo[2.2.1]heptanes: syntheses of (+/-)-epibatidine and (+/-)-epiboxidine.
The syntheses of (+/-)-epibatidine and (+/-)-epiboxidine have been accomplished from commercial 2-methoxy-3,4-dihydro-2H-pyran. A recently developed aza-Prins-pinacol rearrangement was employed for the construction of the key 7-azabicyclo[2.2.1]heptane skeleton of these targets.
Armstrong
Alan
A
Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK. A.Armstrong@imperial.ac.uk
Bhonoah
Yunas
Y
Shanahan
Stephen E
SE
D001372:Aza Compounds / Q000737:chemistry; D053961:Azabicyclo Compounds / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D006536:Heptanes / Q000737:chemistry*; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009842:Oligopeptides / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001372:Aza Compounds; D053961:Azabicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006536:Heptanes; D007555:Isoxazoles; D009842:Oligopeptides; D011725:Pyridines; C414027:aza-pinacol; C106388:epiboxidine; C082748:epibatidine