This short review describes the recent progress made on transition-metal-catalyzed annulative couplings for the synthesis of 3-methyleneisoindolin-1-ones, which are useful intermediates for the synthesis of numerous alkaloids and can be often found in a wide range of natural products and pharmaceuticals. In particular, new one-pot multiple C-C/C-N bond-forming processes for the construction of the 5-methylenepyrrol-2-one nucleus of such compounds are summarized.