Abstract: The Vanderwal group focuses on the total synthesis of bioactive natural products and the development of new methods to support complex synthetic endeavors. Motivated by the structural complexity and biological activity of the dihydro-β-agarofuran (DHBA) family, we aimed to develop an efficient route to access these natural products. Along the way, we established a new method for installing quaternary centers on arene substrates via a diastereoselective Birch reduction/alkylation, using (–)-8-phenylmenthol as an ester chiral auxiliary. Ultimately, we constructed a densely oxygenated tricyclic scaffold through aldol addition and 1,3-dipolar cycloaddition disconnections. This work demonstrates a scalable and concise route toward an advanced intermediate en route to the agarofurans, and lays the groundwork for synthesizing related analogues for future biological evaluation.