Following this time, it was quenched with a saturated, aqueous solution of Na2SO3 (20 mL), and the mixture was transferred to a separatory funnel. The aqueous layer was extracted with EtOAc (2 x 15 mL). The organic layers were collected, dried over Na2SO4, and concentrated under reduced pressure. The resulting residue was purified using a gradient of 0 to 60% EtOAc/hexanes on silica gel to yield 16 (colorless oil, 0.181 g, 0.286 mmol, 69% yield). A 50 mL round-bottom flask was charged with a stir bar, 16 (0.170 g, 0.27 mmol, 1 equiv.), and CH3CN/H2O (2:1 mixture; 6 mL total volume). The reaction flask was cooled to 0 °C using an ice-water bath. NaIO4 (0.115 g, 0.54 mmol, 2 equiv.) and NaHCO3 (0.068 g, 0.81 mmol, 3 equiv.) were added sequentially. The reaction mixture was warmed to room temperature over a period of 2 hours. Following this time, the reaction mixture was filtered through a sintered glass funnel, and the filtrate was transferred to a separatory funnel with 20 mL of H2O. The aqueous layer was extracted with EtOAc (3 x 15 mL). The organic layers were collected, dried over Na2SO4, and concentrated under reduced pressure. The crude product was used in the next step without further purification.