Our laboratory is deeply invested in exploring di-tert-butylsilanols as covalent tethers for the intramolecular installation of hydroxy groups. The triol motif is prevalent in a variety of carbohydrate and polyketide natural products with attractive biological activity (Figure ). We envisioned a ring opening reaction of epoxides by pendant di-tert-butylsilanols, which would form a variety of protected triols. Due to geometric constraints on the transition states of these intramolecular reactions, we reasoned that such openings were likely to be highly regioselective and diastereoselective. Here, we describe our efforts to reduce this concept to practice.