Countless biologically active indole and carbazole alkaloids have been isolated from natural sources.  Indole-2,3-quinodimethane (1) is a reactive intermediate that has been generated by several groups for the synthesis of indole-containing natural products.  However, no stable example of indole-2,3-quinodimethane has been synthesized.  The paper will present our approaches to the generation of potentially stable analogs of indole-2,3-quinodimethane.