1: 90 percent / 70 percent sodium bis(2-methoxyethoxy)aluminum hydride in toluene / benzene / Heating 2: 98 percent / 1,3-dicyclohexylcarbodimide (DCC) / CH2Cl2 / 48 h / Ambient temperature 3: 92 percent / acetic acid; H2O / 1 h / Heating 4: 100 percent / sodium metaperiodate / methanol; H2O / Ambient temperature 5: 100 percent / sodium borohydride / ethanol / 3 h / Ambient temperature 6: 92 percent / pyridine / Ambient temperature 7: 100 percent / sodium metaperiodate / methanol; H2O / Ambient temperature 8: 85 percent / trifluoroacetic anhydride (TFAA) / CH2Cl2 / 576 h / Ambient temperature 9: 100 percent / Raney nickel (W-2) / acetone / 1 h / Heating 10: 1.04 g / K2CO3 / methanol; CH2Cl2 / 0.5 h / Ambient temperature 11: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) triethylamine / 1.) dichloromethane, -60 deg C, 40 min, 2.) dichloromethane, from -60 deg C to RT, 60 min 12: 78 percent / KOH, iodobenzene diacetate / methanol / 3 h / 0 °C 13: 83 mg / 70 percent sodium bis(2-methoxyethoxy)aluminum hydride in toluene / benzene / Heating 14: 85 percent / p-toluenesulfonic acid (PTSA) monohydrate / tetrahydrofuran / 1.5 h / Heating View Scheme

1: 90 percent / sodium bis(2-methoxyethoxy)aluminium (Red-Al) / benzene / Heating 2: 98 percent / DCC / CH2Cl2 / Ambient temperature 3: 92 percent / aq. AcOH / Heating 4: 100 percent / NaBH4 / ethanol / Ambient temperature 5: 92 percent / pyridine / 0 - 20 °C 6: 100 percent / NaIO4 / methanol; ethyl acetate / 0 - 20 °C 7: 85 percent / (CF3CO)2O / CH2Cl2 / 0 - 20 °C 8: 100 percent / Raney-Ni / acetone / Heating 9: K2CO3 / methanol 10: (COCl)2, DMSO / CH2Cl2 / -60 - 20 °C 11: 78 percent / PhI(OAc)2, KOH / 0 °C 12: 83 percent / sodium bis(2-methoxyethoxy)aluminium (Red-Al) / benzene / Heating 13: 85 percent / p-TsOH / tetrahydrofuran / Heating View Scheme