One-Pot Synthesis of Chromone-Fused Pyrrolo[2,1-<i>a</i>]isoquinolines and Indolizino[8,7-<i>b</i>]indoles: Iodine-Promoted Oxidative [2 + 2 + 1] Annulation of <i>O</i>-Acetylphenoxyacrylates with Tetrahydroisoquinolines and Noreleagnines

Abstract

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