hydrogen; Pd/C in ethyl acetate T=20°C; 3 h; atmospheric pressure;

1: 3-methylbut-3-en-1-yl phenyl sulfide With N,N,N',N,-tetramethylethylenediamine; lithium 1-(dimethylamino)naphthalenide in diethyl ether; dimethyl-ether T=-70°C; 2: 1-methyl-4-(methylethenyl)benzene in diethyl ether T=-30 - 20°C; 3: With methanol in diethyl ether T=-78°C; Further stages.;

N,N,N',N,-tetramethylethylenediamine; tert.-butyl lithium in diethyl ether; pentane 1) -78 deg C, 5 min, 2) RT, 2 h;

1.1: 68 percent / benzyltrimethylammonium hydroxide / dioxane / 18 h / 30 - 35 °C 2.1: t-BuOK / toluene / 2 h / Heating 2.2: 62 percent / toluene / 6 °C / Heating 3.1: CuCl / ethanol / 24 h / Heating 4.1: 84 percent / NaBH4 / ethanol / 12 h / 20 °C 5.1: 62 percent / hexane / 0.83 h / Irradiation 6.1: 83 percent / m-chloroperbenzoic acid / CH2Cl2 / 3 h / 20 °C 7.1: 72 percent / dimethylsulfoxide-d6 / 0.02 h / 25 - 200 °C / Irradiation 8.1: 82 percent / H2 / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure View Scheme

1.1: t-BuOK / toluene / 2 h / Heating 1.2: 62 percent / toluene / 6 °C / Heating 2.1: CuCl / ethanol / 24 h / Heating 3.1: 84 percent / NaBH4 / ethanol / 12 h / 20 °C 4.1: 62 percent / hexane / 0.83 h / Irradiation 5.1: 83 percent / m-chloroperbenzoic acid / CH2Cl2 / 3 h / 20 °C 6.1: 72 percent / dimethylsulfoxide-d6 / 0.02 h / 25 - 200 °C / Irradiation 7.1: 82 percent / H2 / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure View Scheme

1: 95 percent / Na2CO3 / ethanol / 96 h / Heating 2: 62 percent / hexane / 0.83 h / Irradiation 3: 83 percent / m-chloroperbenzoic acid / CH2Cl2 / 3 h / 20 °C 4: 72 percent / dimethylsulfoxide-d6 / 0.02 h / 25 - 200 °C / Irradiation 5: 82 percent / H2 / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure View Scheme

1.1: 98 percent / AlCl3; HCl / H2O / 60 °C 2.1: 68 percent / benzyltrimethylammonium hydroxide / dioxane / 18 h / 30 - 35 °C 3.1: t-BuOK / toluene / 2 h / Heating 3.2: 62 percent / toluene / 6 °C / Heating 4.1: CuCl / ethanol / 24 h / Heating 5.1: 84 percent / NaBH4 / ethanol / 12 h / 20 °C 6.1: 62 percent / hexane / 0.83 h / Irradiation 7.1: 83 percent / m-chloroperbenzoic acid / CH2Cl2 / 3 h / 20 °C 8.1: 72 percent / dimethylsulfoxide-d6 / 0.02 h / 25 - 200 °C / Irradiation 9.1: 82 percent / H2 / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure View Scheme

titanium tetrachloride in dichloromethane; toluene T=0°C; Reetz methylation; 24 h;

1: 1.) O3, 2.) Me2S / 1.) CH2Cl2, 2.) -78 deg C 2: acetone / Jones oxidation 3: H2SO4 / Heating 4: benzene / 0 °C 5: 85 percent / ZnI2 / 1,2-dichloro-ethane / Ambient temperature 6: 1.) i-Pr2NLi, HCO2Et, 2.) p-MeC6H4SO2N3, Et3N / 1.) THF, -78 deg C, 2.) CH2Cl2, r.t. 7: Rh2(OAc)4 / benzene / Heating 8: m-ClC6H4CO3H, aq. NaHCO3 / CH2Cl2 / Ambient temperature 9: NiCl2*6H2O, NaBH4 / methanol / Ambient temperature 10: i-Pr2NLi, HMPA / tetrahydrofuran / Ambient temperature 11: LiAlH4 / diethyl ether / Ambient temperature 12: pyridinium chlorochromate / CH2Cl2 / Ambient temperature 13: H2NNH2*H2O, Na / ethane-1,2-diol; bis-(2-hydroxy-ethyl) ether / 185 °C View Scheme

1: H2SO4 / Heating 2: benzene / 0 °C 3: 85 percent / ZnI2 / 1,2-dichloro-ethane / Ambient temperature 4: 1.) i-Pr2NLi, HCO2Et, 2.) p-MeC6H4SO2N3, Et3N / 1.) THF, -78 deg C, 2.) CH2Cl2, r.t. 5: Rh2(OAc)4 / benzene / Heating 6: m-ClC6H4CO3H, aq. NaHCO3 / CH2Cl2 / Ambient temperature 7: NiCl2*6H2O, NaBH4 / methanol / Ambient temperature 8: i-Pr2NLi, HMPA / tetrahydrofuran / Ambient temperature 9: LiAlH4 / diethyl ether / Ambient temperature 10: pyridinium chlorochromate / CH2Cl2 / Ambient temperature 11: H2NNH2*H2O, Na / ethane-1,2-diol; bis-(2-hydroxy-ethyl) ether / 185 °C View Scheme