The synthesis of simple nortropane and nortrop-6-ene derivatives from cyclohepta-1,3-diene is described. The key intermediates are trans-1-amino-4-chloro-cycloheptanes and -cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation. Corresponding derivatisation of cyclohexa- and cycloocta-1,3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of 1-amino-4-acetoxy-derivatives is described. Nitrogen inversion data for selected nortropane derivatives are included.
|Number of pages||18|
|Publication status||Published - 8 Jan 1993|