<p dir="ltr">Dihydro-β-agarofurans are a class of polyester sesquiterpene secondary metabolites isolated from the <i>Celastraceae</i> plant family. Many compounds in this class have demonstrated biological activity and have therefore generated much synthetic interest. However, their <i>trans</i>-decalin/tetrahydrofuranyl ring system and high levels of oxidation make them synthetically challenging. The first chapter presents a discussion on the biological activity and various historical methods used to construct this ring system. The second chapter describes the new dearomative oxidation/cyclization method developed by our group to rapidly synthesize the tricyclic ring system in only 9 steps from commercially available 6-methoxy-1-tetralone. Other key steps include a MHAT reduction of a b,b-disubstituted dienone, stereospecific reduction of an enone, and hydroxyl-directed Simmons-Smith cyclopropanation. The large-scale synthesis of these advanced synthetic intermediates and the attempted elaboration to the dihydro-β-agarofuran core is described in detail.</p>