Since its isolation from the Celastraceae vine Tripterygium wilfordii Hook in 1953, (-)-euonyminol remains the most highly oxygenated dihydro-??-agarofuran core found in a variety of bioactive Celastraceae natural products, including hypoglaunine B and hyponine B, both of which had been identified as potential anti-HIV agents. This thesis contains an overview of the natural products of the Celastraceae family and the wide spectrum of interesting biological activity that they display, with particular focus upon anti-HIV properties. Prior synthetic work towards euonyminol and background synthetic studies towards the construction of related decalin scaffolds via ring closing metathesis are also described. The remainder of this thesis describes the efforts made towards the total synthesis of (-)-euonyminol via both a two-directional method and an alternative ring-opening-ring-closing metathesis approach, the viability of which was proven using model systems.