The silver ion induced rearrangement of n-chloro-octahydropyrindines : a sythesis of monomorine I

The effect of treating N-chloro-octahydro-1-pyrindines with silver tetrafluoroborate and subsequent hydride or trapping of the imminium ion intermediate results in good yields of indolizidines. The rearrangement of N-chloro-octahydro-1-pyrindine to indolizidine seems independent of a cis or trans fussion of the pyrindine rings and occurs with preference over alkyl substituent migration in the C-2 substituted case. Efficient trapping with cyanide and utilization of the chemistry this functionality provides led to a synthesis of monorine I.