1: 71 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 2: 0.055 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C 3: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 4: 0.052 g / NaBH4 / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 5: 94 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 6: 92 percent / HF*pyridine / tetrahydrofuran / 2 h / 0 - 20 °C 7: 97 percent / 3,3-dimethyldioxirane / CH2Cl2; acetone / 2.5 h / -78 - -50 °C View Scheme

1: 71 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 2: 0.055 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C 3: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 4: 0.052 g / NaBH4 / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 5: 94 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 6: 92 percent / HF*pyridine / tetrahydrofuran / 2 h / 0 - 20 °C View Scheme