Poly(ADP-ribose) polymerase (PARP) represents a large family of enzymes that are activated upon DNA breakage, which are then involved in a cascade of reactions that eventually lead to cell death. PARPs, known to cause a variety of damage to the human body, are targets of many researches’ investigating potential inhibition mechanisms. To this point, plenty of PARP inhibitors have been synthesized and tested for potency against many diseases. Some have great potency against particular diseases, while others are already being used as drugs. The current research suggests a potential synthesis of novel PARP inhibitors, to be accomplished through Diels-Alder chemistry. The proposed compounds consist of an isoindolinone core bearing different functional groups. Three different strategies are described for the synthesis of the novel PARP inhibitors and all protocols involve sulfur dioxide extrusion chemistry to create a diene, the desired transient starting material. The diene is envisioned further to be reacted with a variety of dienophiles to give possibly potential PARP inhibitors. / NSERC