1: 72 percent / CAN / ethanol; H2O / -40 - 0 °C 2: Na2S2O4 / CHCl3; H2O / Ambient temperature 3: Me3SiBr / CH2Cl2 / 0.17 h / Heating 4: AcOK / ethanol / 0.33 h / Ambient temperature 6: 85 percent / tetrahydrofuran / 0.5 h / Ambient temperature 7: 85 percent / DDQ, CSA / benzene / 5 h / Heating 8: 87 percent / 1N HCl / 12 h / Heating View Scheme

With  lithium aluminium tetrahydride in  diethyl ether 1 h;  Heating;   

Multi-step reaction with 5 steps 1: 98 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature2: 95 percent / DMSO, Et3N / CH2Cl2 / -60 deg C then warming up to 0 deg C3: DIBAL / toluene / 0.33 h / -78 °C4: 90 percent / (i-Pr)2NEt / tetrahydrofuran / 3 h / Heating5: 94 percent / LiAlH4 / diethyl ether / 1 h / Heating  

Multi-step reaction with 4 steps 1: 95 percent / DMSO, Et3N / CH2Cl2 / -60 deg C then warming up to 0 deg C2: DIBAL / toluene / 0.33 h / -78 °C3: 90 percent / (i-Pr)2NEt / tetrahydrofuran / 3 h / Heating4: 94 percent / LiAlH4 / diethyl ether / 1 h / Heating  

Multi-step reaction with 3 steps 1: DIBAL / toluene / 0.33 h / -78 °C2: 90 percent / (i-Pr)2NEt / tetrahydrofuran / 3 h / Heating3: 94 percent / LiAlH4 / diethyl ether / 1 h / Heating  

Multi-step reaction with 2 steps 1: 90 percent / (i-Pr)2NEt / tetrahydrofuran / 3 h / Heating2: 94 percent / LiAlH4 / diethyl ether / 1 h / Heating  

Multi-step reaction with 2 steps 1: 72 percent / CAN / ethanol; H2O / -40 - 0 °C2: Na2S2O4 / CHCl3; H2O / Ambient temperature  

Multi-step reaction with 4 steps 1: 72 percent / CAN / ethanol; H2O / -40 - 0 °C2: Na2S2O4 / CHCl3; H2O / Ambient temperature3: Me3SiBr / CH2Cl2 / 0.17 h / Heating4: AcOK / ethanol / 0.33 h / Ambient temperature