1: 100 percent / L-Selectride / tetrahydrofuran / -40 - -30 °C 2: 89 percent / i-Pr2NEt / CH2Cl2 / 20 h / Ambient temperature 3: 94 percent / H2 / Raney Ni (W2) / ethanol / 72 h / 760 Torr 4: 88 percent / i-Pr2NEt / CH2Cl2 / -40 - -20 °C 5: HF*pyridine / tetrahydrofuran / 60 h / Ambient temperature 6: i-Pr2NEt / CH2Cl2 / 0.5 h / -40 - -20 °C 7: DIBAL-H / CH2Cl2; hexane / 0.5 h / -78 °C 8: DMAP / toluene / 12 h / 50 °C 9: 76 percent / DDQ / CH2Cl2; H2O / 1.5 h / Ambient temperature 10: 87 percent / TPAP, NMO, MS4A / acetonitrile / 1 h / Ambient temperature 11: 1.) NBS, 2.) CrO3, H2SO4 / 1.) THF, phosphate buffer pH 7, 0 deg C, 15 min, 2.) acetone, 0 deg C, 15 min 12: MS 4A, PPC / CH2Cl2 / 12 h / Ambient temperature 13: HF*pyridine / tetrahydrofuran / Ambient temperature View Scheme