229958-72-9Relevant academic research and scientific papers
Conformationally constrained nicotines. 1-Pyridinyl-7- azabicyclo[2.2.1]heptane and 1-pyridinyl-8-azabicyclo[3.2.1] octane analogues
Xu, Ying-Zi,Choi, Jaesung,Isabel Calaza,Turner, Sean,Rapoport, Henry
, p. 4069 - 4078 (1999)
Conformationally constrained bicyclo analogues of natural (-)-nicotine and unnatural (+)-nicotine have been synthesized from D- and L-glutamic acid, respectively. Regioselective addition of 3-lithiopyridine to the γ-carbonyl of a protected glutamate was followed by intramolecular imine formation and stereospecific catalytic hydrogenation of the resultant pyrroline to give cis-5-pyridinylproline. A sequence of transformations to convert the ester to bromide was followed by the key intramolecular anionic cyclization at the benzylic position to form the 1-pyridinyl-7-azabicyclo[2.2.1]heptane analogue. Alternatively, homologation of the ester of cis-5-pyridinylproline and conversion to bromide allowed cyclization to the 1-pyridinyl-7- azabicyclo[3.2.1]octane analogues.
