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A highly concise stereoselective synthesis of a newly identified alkaloid with a pyrroloindoloquinazoline skeleton has been achieved. To this end, a chiral auxiliary mediated asymmetric acetate aldol reaction on tryptanthrin was explored and the resulting adduct was converted to the product by a novel one-pot reductive cyclization/transamidation using NiCl2·6H2O/NaBH4 in methanol.

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An efficient, eco-friendly, base free, one-pot, sequential protocol was developed for epoxide azidolysis and copper-catalyzed azide-alkyne cycloaddition using water as the solvent for the synthesis of 3-hydroxy-1-alkyl-3-[(4-aryl/alkyl-1H-1,2,3-triazol-1-yl)methyl]indolin-2-ones. The optimized reaction conditions have been generalized in the case of aromatic as well as aliphatic alkyne partners to afford good yields and high regioselectivity.