Aplydactone is a sesquiterpene natural product isolated from the sea hare Aplysia dactylomela that isfound on the northern coast of Madagascar. Interest in synthesizing aplydactone is driven by its extremely novel and conformationally strained tetracyclic framework. Aplydactone’s ring system has bond angles more acute than ever before seen for cyclobutane. Additionally, the carbon-carbon bonds in aplydactone’s cyclobutane rings are reported to be longer than average carbon-carbon bonds. This work describes the initial synthetic work toward a model study of aplydactone in order to provide insight into the compound’s biomimetic pathway as well as strategies for the synthesis of similar structures.