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.
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Armstrong et al. (2007) studied this question.
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