Cycloaddition reactions for the synthesis of piperidine and indolizidine alkaloids

Abstract

The intramolecular nitrone dipolar cycloaddition of N-alkenylnitrones has been utilised in approaches to the synthesis of a family of indolizidines such as castanospermine and a tethered swainsonine analogue. Examples of a tandem hydroxylamino-alkyne cyclisation/dipolar trapping experiment in the synthesis of (±)-adaline and (±)-euphococcinine are outlined.