合成路线1

10) Albertini et al. reported a formal synthesis of epibatidine utilizing the enantiopure cyclohexanone (XXXVIII) as a convenient starting material which was easily available from D-(-)quinic acid (XXXVII). An important step in this synthesis was the regioselective intramolecular nucleophilic ring opening of the vicinal diol cyclic sulfate (XXXIX). When (XXXIX) was subjected to hydrogenation, the azido group was converted into an amino group and an internal displacement took place spontaneously to form the inner salt (XL). Three standard manipulations furnished the optically pure ketone (VIII), which had already been converted to epibatidine as described by Fletcher and coworkers.