1: 83 mg / 70 percent sodium bis(2-methoxyethoxy)aluminum hydride in toluene / benzene / Heating 2: 85 percent / p-toluenesulfonic acid (PTSA) monohydrate / tetrahydrofuran / 1.5 h / Heating View Scheme

1: 86 percent / LAH 2: 91 percent / p-TsOH / tetrahydrofuran View Scheme

With  iodosylbenzene T=0°C;   

Multi-step reaction with 16 steps 1: 100 percent / triton B / tetrahydrofuran; 2-methyl-propan-2-ol / 48 h / Ambient temperature2: 81 percent / zinc, conc. HCl / ethanol / 15 h / Heating3: 1.) osmium tetraoxide, 2.) sodium metaperiodate / 1.) THF, water, 0 deg C, 5 min, 2.) THF, water, 1.5 h4: 100 percent / p-toluenesulfonic acid (PTSA) / CH2Cl2 / 3 h / Heating5: 90 percent / 70 percent sodium bis(2-methoxyethoxy)aluminum hydride in toluene / benzene / Heating6: 98 percent / 1,3-dicyclohexylcarbodimide (DCC) / CH2Cl2 / 48 h / Ambient temperature7: 92 percent / acetic acid; H2O / 1 h / Heating8: 100 percent / sodium metaperiodate / methanol; H2O / Ambient temperature9: 100 percent / sodium borohydride / ethanol / 3 h / Ambient temperature10: 92 percent / pyridine / Ambient temperature11: 100 percent / sodium metaperiodate / methanol; H2O / Ambient temperature12: 85 percent / trifluoroacetic anhydride (TFAA) / CH2Cl2 / 576 h / Ambient temperature13: 100 percent / Raney nickel (W-2) / acetone / 1 h / Heating14: 1.04 g / K2CO3 / methanol; CH2Cl2 / 0.5 h / Ambient temperature15: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) triethylamine / 1.) dichloromethane, -60 deg C, 40 min, 2.) dichloromethane, from -60 deg C to RT, 60 min16: 78 percent / KOH, iodobenzene diacetate / methanol / 3 h / 0 °C  

With  lithium aluminium tetrahydride