1: 1.) osmium tetraoxide, 2.) sodium metaperiodate / 1.) THF, water, 0 deg C, 5 min, 2.) THF, water, 1.5 h 2: 100 percent / p-toluenesulfonic acid (PTSA) / CH2Cl2 / 3 h / Heating 3: 90 percent / 70 percent sodium bis(2-methoxyethoxy)aluminum hydride in toluene / benzene / Heating 4: 98 percent / 1,3-dicyclohexylcarbodimide (DCC) / CH2Cl2 / 48 h / Ambient temperature 5: 92 percent / acetic acid; H2O / 1 h / Heating 6: 100 percent / sodium metaperiodate / methanol; H2O / Ambient temperature 7: 100 percent / sodium borohydride / ethanol / 3 h / Ambient temperature 8: 92 percent / pyridine / Ambient temperature 9: 100 percent / sodium metaperiodate / methanol; H2O / Ambient temperature 10: 85 percent / trifluoroacetic anhydride (TFAA) / CH2Cl2 / 576 h / Ambient temperature 11: 100 percent / Raney nickel (W-2) / acetone / 1 h / Heating 12: 1.04 g / K2CO3 / methanol; CH2Cl2 / 0.5 h / Ambient temperature 13: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) triethylamine / 1.) dichloromethane, -60 deg C, 40 min, 2.) dichloromethane, from -60 deg C to RT, 60 min 14: 78 percent / KOH, iodobenzene diacetate / methanol / 3 h / 0 °C 15: 83 mg / 70 percent sodium bis(2-methoxyethoxy)aluminum hydride in toluene / benzene / Heating 16: 85 percent / p-toluenesulfonic acid (PTSA) monohydrate / tetrahydrofuran / 1.5 h / Heating View Scheme

1: 100 percent / OsO4, NaIO4 / tetrahydrofuran; H2O / 0 - 20 °C 2: 100 percent / p-TsOH / 1,2-dichloro-ethane / Heating 3: 90 percent / sodium bis(2-methoxyethoxy)aluminium (Red-Al) / benzene / Heating 4: 98 percent / DCC / CH2Cl2 / Ambient temperature 5: 92 percent / aq. AcOH / Heating 6: 100 percent / NaBH4 / ethanol / Ambient temperature 7: 92 percent / pyridine / 0 - 20 °C 8: 100 percent / NaIO4 / methanol; ethyl acetate / 0 - 20 °C 9: 85 percent / (CF3CO)2O / CH2Cl2 / 0 - 20 °C 10: 100 percent / Raney-Ni / acetone / Heating 11: K2CO3 / methanol 12: (COCl)2, DMSO / CH2Cl2 / -60 - 20 °C 13: 78 percent / PhI(OAc)2, KOH / 0 °C 14: 83 percent / sodium bis(2-methoxyethoxy)aluminium (Red-Al) / benzene / Heating 15: 85 percent / p-TsOH / tetrahydrofuran / Heating View Scheme