Synthesis of (±)tylophorine by the intramolecular cycloaddition of an azide with an ω-chloroalkene

Article abstract of DOI:10.1016/S0040-4020(01)89538-7

Cyclization of (Z)-1-(2-chloromethyl)phenyl-5-azidopent-1-ene 10 in benzene at 120°C followed by treatment with sodium borohydride produced 1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinoline 11 in 71% yield. A similar cyclization of (Z)-2,3,6,7-tetrametho