Bicyclo[3.3.1]nonanes as synthetic intermediates. Part 20.1 Asymmetric synthesis of the indolizidine alkaloids monomorine I and indolizidine 223AB

Abstract

Total syntheses of the indolizidine alkaloids monomorine I and indolizidine 223AB have been achieved by starting from the chiral cis-2,5-disubstituted pyrrolidine or cis-2,6-disubstituted piperidine obtained from the asymmetric cleavage of 8-azabicyclo[3.2.1]octan-3-one or 9-azabicyclo[3.3.1]nonan-3-one at the ‘fork head’.