1: 93 percent / DIBAL-H / toluene / 0.5 h / -80 °C 2: 89 percent / NaN(SiMe3)2 / tetrahydrofuran / 2 h / -80 - 20 °C 3: 92 percent / NH4F / tetrahydrofuran; methanol / 4 h 4: 97 percent / pyridine / 1 h / 20 °C 5: 83 percent / 3 percent HCl in MeOH / diethyl ether / 20 °C 6: periodinane / CH2Cl2 / 2 h / 20 °C 7: 75 percent / NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / 20 °C 8: 85 percent / (S)-BINAL-H / 2 h / -100 °C 9: 1N aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme