260269-91-8Relevant academic research and scientific papers
Enantiospecific synthesis of annulated nicotine analogues from D- and L- glutamic acid. Pyridotropanes
Turner, Sean C.,Zhai, Hongbin,Rapoport, Henry
, p. 861 - 870 (2000)
The conformationally restricted nicotinoid 1-methyl-8- azabicyclo[3.2.1]octano[2,3-c]pyridine, pyrido[3,4-b]tropane, has been prepared enantiospecifically from both D- and L-glutamic acid. The method involved coupling of pyroglutamic acid derivatives with ortho-lithiated 4- chloropyridine, followed by intramolecular imine formation and reduction to generate the D- and L-5-substituted proline esters. Chloro-iodo exchange and side chain extension gave the precursor for the [3.2.1] system. Construction of the 8-azabicyclo[3.2.1]octano-[2,3-c]pyridine framework was achieved by an intramolecular Heck reaction. Subsequent ozonolysis gave the ketone which was reduced to the carbinol or methylene, yielding the fused nicotine analogues.
