1: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) reflux 2: 99 percent / diethyl ether / Ambient temperature 3: 88 percent / Et3N, TMSOTf / CH2Cl2 / 16 h / Heating 4: 97 percent / Dess-Martin periodinane reagent / CH2Cl2 / Ambient temperature 5: 91 percent / AgNO3, CaCO3 / acetone; H2O / Ambient temperature 6: 90 percent / DIBAH / diethyl ether / 0 °C 7: 41 percent / AgNO3 / acetone; H2O / 24 h / 40 °C View Scheme

1: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) reflux 2: 99 percent / diethyl ether / Ambient temperature 3: 88 percent / Et3N, TMSOTf / CH2Cl2 / 16 h / Heating 4: 97 percent / Dess-Martin periodinane reagent / CH2Cl2 / Ambient temperature 5: 91 percent / AgNO3, CaCO3 / acetone; H2O / Ambient temperature 6: 90 percent / DIBAH / diethyl ether / 0 °C 7: 54 percent / AgNO3 / acetone; H2O / 24 h / 40 °C View Scheme