Formal synthesis of natural epibatidine and of its enantiomer: Use of radical cyclization in an enantiospecific route

Article abstract of DOI:10.1016/S0040-4039(98)00958-7

(S)-Pyroglutamic acid was converted into the (phenylthio)acetylene 14, which undergoes radical cyclization to the 7-azabicyclo[2.2.1]heptane 15. Ozonolysis then affords ketone 4, a synthetic precursor of (-)-epibatidine.