potassium carbonate in acetone 1 h; Heating;

sodium hydroxide in methanol 1 h; Ambient temperature;

1: 75 percent / silica gel, aq. NaOH / methanol / 2 h / Ambient temperature 2: 91 percent / K2CO3 / acetone / 1 h / Heating View Scheme

1: 65 percent / H2SO4 / CH2Cl2 / 0.17 h 2: 75 percent / silica gel, aq. NaOH / methanol / 2 h / Ambient temperature 3: 91 percent / K2CO3 / acetone / 1 h / Heating View Scheme

tert.-butyl lithium 1.) THF, -78 deg C, 2.) -78 deg C to room temp.;

1: 71 percent / NaOMe / methanol / 4 °C 2: xylene / Heating 3: LiAlH4 / diethyl ether / Heating 4: 84 percent / MnO2 / CH2Cl2 / Heating 5: 70 percent / (Ph3P)2Rh(CO)Cl, 1,3-bis(diphenylphosphino)propane / 1,3,5-trimethyl-benzene / Heating 6: 57 percent / 1.) t-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C to room temp. View Scheme

1: LiAlH4 / diethyl ether / Heating 2: 84 percent / MnO2 / CH2Cl2 / Heating 3: 70 percent / (Ph3P)2Rh(CO)Cl, 1,3-bis(diphenylphosphino)propane / 1,3,5-trimethyl-benzene / Heating 4: 57 percent / 1.) t-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C to room temp. View Scheme

1: 98 percent / KOH / ethanol / 4.25 h / Heating 2: 79 percent / bromine, sodium acetate / acetic acid / Ambient temperature; 1.) 22 h, 2.) 24 h, 3.) 20 h 3: 71 percent / NaOMe / tetrahydrofuran; methanol / 1.) -5 deg C, 5 h, 2.) 4 deg C, 48 h 4: xylene / 1 h / Heating 5: LiAlH4 / diethyl ether / 1.) 4 h, reflux, 2.) overnight, RT 6: 84 percent / MnO2 / CH2Cl2 / 0.75 h / Heating 7: 70 percent / Rh(PPh3P)2CO(Cl), 1,3-bis(diphenylphosphino)propane / 1,3,5-trimethyl-benzene / 1.3 h / Heating 8: 1.) 1.8 M t-butyl-lithium / 1.) THF, hexane, -78 deg C, 1 h; 2.) THF, hexane, -78 deg C, 1 h View Scheme

1: 98 percent / KOH / ethanol / 4.25 h / Heating 2: 79 percent / bromine, sodium acetate / acetic acid / Ambient temperature; 1.) 22 h, 2.) 24 h, 3.) 20 h 3: 71 percent / NaOMe / tetrahydrofuran; methanol / 1.) -5 deg C, 5 h, 2.) 4 deg C, 48 h 4: xylene / 1 h / Heating 5: LiAlH4 / diethyl ether / 1.) 4 h, reflux, 2.) overnight, RT 6: 84 percent / MnO2 / CH2Cl2 / 0.75 h / Heating 7: 70 percent / Rh(PPh3P)2CO(Cl), 1,3-bis(diphenylphosphino)propane / 1,3,5-trimethyl-benzene / 1.3 h / Heating 8: 1.) 1.8 M t-butyl-lithium / 1.) THF, hexane, -78 deg C, 1 h; 2.) THF, hexane, -78 deg C, 1 h View Scheme

1: 79 percent / bromine, sodium acetate / acetic acid / Ambient temperature; 1.) 22 h, 2.) 24 h, 3.) 20 h 2: 71 percent / NaOMe / tetrahydrofuran; methanol / 1.) -5 deg C, 5 h, 2.) 4 deg C, 48 h 3: xylene / 1 h / Heating 4: LiAlH4 / diethyl ether / 1.) 4 h, reflux, 2.) overnight, RT 5: 84 percent / MnO2 / CH2Cl2 / 0.75 h / Heating 6: 70 percent / Rh(PPh3P)2CO(Cl), 1,3-bis(diphenylphosphino)propane / 1,3,5-trimethyl-benzene / 1.3 h / Heating 7: 1.) 1.8 M t-butyl-lithium / 1.) THF, hexane, -78 deg C, 1 h; 2.) THF, hexane, -78 deg C, 1 h View Scheme