Rahul Balu Dadhe, Hemalatha Talluru, Srihari Pabbaraja, Goverdhan Mehta
We delineate a viable, tandem annulation strategy for accessing indoloindolizines. This one-pot, transition-metal-free approach involves the stitching of preformed 2-methyl-3-nitro/3-carbonyl-1H-indoles with assorted ynones through sequential aza-Michael addition and a vinylogous aldol condensation reaction cascade. The protocol displays high regioselectivity and broad substrate scope, providing concise access to a diverse library with 24 examples. This has further enabled access to two analogues of marine-derived alkaloid homofascaplysin C (a red pigment) exhibiting selective anti-cancer activity.