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Indole, a p-nucleophile, reacts with Brønsted acid activated imide carbonyl group in an intramolecular fashion via a 6-exo-trig cyclization, to deliver a condensed tetrahydro-b-carboline unit. This methodology is effectively applied to assemble the tetrahydro-b-carboline skeleton containing alkaloids such as harmicine and 10-desbromoarborescidine-A.

The regio and diastereoselective synthesis of 1 or 2 alkylsubstituted pyrroloisoquinolinones and indolizinoindolones by triflic acid mediated cyclization via an electrophilic activation of unsymmetrical succinimide carbonyl groups followed by the reduction of fused cyclic N-acyliminium ion is reported. This strategy successfully furnished the pyrroloisoquinolinone and indolizinoindolone derivatives in regioand diastereoselective manner. The steric factor dictates the regioselectivity in N-phenethyl unsymmetrical succinimides and electronic factor seems to dictate the regioselectivity in N-(3-indolylethyl) unsymmetrical succinimides.

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