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Abstract
The use of dimethyl quinolinate (1) in the general scheme of alkaloid synthesis,2 based on the two-step process of hydrogenation of β-acylpyridines or their N-alkyl salts and acid-catalyzed cyclization of the resultant 2-piperideines, has been foiled by its steric inhibition to N-alkylation and its uncontrollable hydrogenation leading to 2a. 3 Since, however, the tetrahydropyridines 3, thus unattainable by traditional means from 1, appeared to be excellent intermediates on route to angularly substituted quinolizidines and, hence, to complex alkaloids, a study of their preparation from 2a was undertaken.