A novel approach to conformationally restricted analogues of nicotine and anabasine by an intramolecular Hamaguchi–Ibata reaction

A short synthesis of methyl (SR)-8,10-dichloro-1,2,3,4,5,6-hexahydro-6-hydroxy-1-methyl-1,9-phenanthroline-6-carboxylate (14) has been achieved en route to conformationally restricted analogues of nicotine and anabasine. The key feature of this process involves an efficient intramolecular Hamaguchi–Ibata reaction of 11.