Studies directed toward the study and treatment for cocaine addiction include the evaluation of potent analogs possessing the azabicyclo[3.2.1]octane (tropane) ring system. The asymmetric synthesis of the closely related azabicyclo[3.2.2]nonane skeleton is proposed via rhodium catalyzed decomposition of vinyldiazomethanes in the presence of suitably protected, chiral 1,2-dihydropyridines. Conversion of these molecules to similarly substituted analogs of proven biologically active tropanes will be carried out using established procedures. It is proposed that these molecules will possess a high overall degree of affinity for the serotonin and/or dopamine-based receptors, complementing the activity of known biologically active tropanes. It is the intent that the synthesis and study of these compounds will prove valuable toward the further understanding and treatment of certain types of drug addiction.
