Copper-catalyzed synthesis of a highly hydroxy functionalized benzo[e]indolizidine by intramolecular N-arylation

The enantiopure (2S,3S,3aS,5S)-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-2,3,5-triol (2,3,5-trihydroxybenzo[e]indolizidine) framework has been synthesized by a straightforward strategy consisting of 1,3-dipolar cycloaddition of a pyrroline N-oxide to 2-bromostyrene followed by isoxazolidine N–O bond reduction and cyclization by copper-catalyzed nucleophilic aromatic substitution of the intermediate pyrrolidine.