We describe an enantioselective total synthesis of the nonahydroxylated sesquiterpenoid euonyminol, the dihydro-flagarofuran nucleus of the macrocyclic terpenoid alkaloids known as the cathedulins. Key features of the synthetic sequence include a highly diastereoselective intramolecular alkene oxyalkylation to establish the C10 quaternary center, an intramolecular aldol-dehydration to access the tricyclic scaffold of the target, a tandem lactonization-epoxide opening to form the trans-C2-C3 vicinal diol residue, and a late-stage diastereoselective a-ketol rearrangement. The synthesis provides the first synthetic access to enantioenriched euonyminol and establishes a platform to synthesize the cathedulins.