An iodine-promoted one-pot cascade oxidative annulation reaction has been developed for the synthesis of chromone-fused-pyrrolo[2,1-a]isoquinolines and indolizino[8,7-b]indoles from o-acetylphenoxyacrylates, tetrahydroisoquinolines, and noreleagnines. This process underwent a logical approach to both chromone-fused-pyrrolo[2,1-a]isoquinolines and chromone-fused-indolizino[8,7-b]indoles isolamellarin derivatives. Manipulations of l-menthol and dl-α-tocopherol demonstrate the applications of this strategy.