Starting from dimethyl 3,4-methylenedioxyhomophthalate, a concise total synthesis of oxyavicine has been described via the base catalyzed monoalkylation, homophthalimide formation, oxidative selective iodination, regioselective reductive dehydration and an intramolecular Heck coupling reaction followed by the oxidation pathway with 16% overall yield in six steps.