Highly regio- and diastereo-selective synthesis of novel tri- and tetra-cyclic perhydroquinoline architectures via an intramolecular [3 + 2] cycloaddition reactionElectronic supplementary information (ESI) available: Representative experimental procedures, with all spectral data of 9a-k, 12a-g, 15a-d, 17a-d, crystal data, ORTEP diagram. CCDC 764210 for 9e, 833470 for 12a and 976506 for 15b. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ob02203c

A facile and efficient synthetic protocol was established for the construction of novel tri- and tetra-cyclic pyrrolo/pyrrolizinoquinoline architectures via the in situ formation of azomethine ylide followed by an intramolecular [3 + 2] cycloaddition reaction strategy. This protocol leads to the creation of two/three new rings and three/four contiguous stereocentres, in which one of them is a tetra-substituted carbon center, in a highly diastereoselective fashion with excellent yields. A facile and efficient synthetic protocol was established for the construction of novel tri- and tetra-cyclic pyrrolo/pyrrolizinoquinoline architectures via an intramolecular [3 + 2] cycloaddition reaction strategy.