1: p-TsOH / benzene / 16 h / Heating 2: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 10 min, 2.) -78 deg C to room t. 3: Jones reagent / acetone / 0.5 h / 0 °C 4: 87.2 percent / 95 percent H2SO4 / 5 h / Heating 5: 75 percent / diethyl ether; toluene / 0.5 h / -78 °C 6: 81.5 percent / ZnI2 / 1,2-dichloro-ethane / 0.17 h / Ambient temperature 7: 1.) BuLi(hexane), (i-Pr)2NH / 1.) THF, -78 deg C, 1 h 2.) THF, -78 deg C, 1 h, to room t. 8: 100 percent / p-MeC6H4SO2N3, Et3N / CH2Cl2 / 4 h / Ambient temperature 9: multistep reaction; reactions under var. conditions <Rh(OAc)2, Cu(acac)2, R-1648 catalist> 10: 90 percent / NaBH4, NiCl2*6H2O / methanol / 24 h / Ambient temperature 11: 1.) BuLi(hexane), (i-Pr)NH / 1.) HMPA, THF, 0 deg C, 2 h, 2.) HMPA, THF, 0 deg C to room t., 2 h 12: 91.2 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 13: 92.3 percent / PCC / CH2Cl2 / 3 h / Ambient temperature 14: 1.) 80 percent N2H4*H2O, 2.) Na / 1.) diethylene glycol, ethyleneglycol, 184 deg C, 1.5 h, 2.) diethylene glycol, ethyleneglycol, 70 deg C, then 4 h, reflux View Scheme

1: 1.) Mg / 1.) THF, room t., 2.) THF, room t., 1 h 2: p-TsOH / benzene / 16 h / Heating 3: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 10 min, 2.) -78 deg C to room t. 4: Jones reagent / acetone / 0.5 h / 0 °C 5: 87.2 percent / 95 percent H2SO4 / 5 h / Heating 6: 75 percent / diethyl ether; toluene / 0.5 h / -78 °C 7: 81.5 percent / ZnI2 / 1,2-dichloro-ethane / 0.17 h / Ambient temperature 8: 1.) BuLi(hexane), (i-Pr)2NH / 1.) THF, -78 deg C, 1 h 2.) THF, -78 deg C, 1 h, to room t. 9: 100 percent / p-MeC6H4SO2N3, Et3N / CH2Cl2 / 4 h / Ambient temperature 10: multistep reaction; reactions under var. conditions <Rh(OAc)2, Cu(acac)2, R-1648 catalist> 11: 90 percent / NaBH4, NiCl2*6H2O / methanol / 24 h / Ambient temperature 12: 1.) BuLi(hexane), (i-Pr)NH / 1.) HMPA, THF, 0 deg C, 2 h, 2.) HMPA, THF, 0 deg C to room t., 2 h 13: 91.2 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 14: 92.3 percent / PCC / CH2Cl2 / 3 h / Ambient temperature 15: 1.) 80 percent N2H4*H2O, 2.) Na / 1.) diethylene glycol, ethyleneglycol, 184 deg C, 1.5 h, 2.) diethylene glycol, ethyleneglycol, 70 deg C, then 4 h, reflux View Scheme

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

1: 92 percent / lithium / tetrahydrofuran / 0.83 h / 15 - 20 °C / sonication 2: 100 percent / second generation Grubbs catalyst / benzene / 0.5 h / Heating 3: 77 percent / p-toluenesulfonic acid / benzene / 4 h / Heating View Scheme

1: 100 percent / second generation Grubbs catalyst / benzene / 0.5 h / Heating 2: 77 percent / p-toluenesulfonic acid / benzene / 4 h / Heating View Scheme

1.1: potassium tert-amyl oxide / benzene / 0.17 h / 0 - 20 °C 1.2: 90 percent / benzene / 0.5 h / 0 °C 2.1: 92 percent / lithium / tetrahydrofuran / 0.83 h / 15 - 20 °C / sonication 3.1: 100 percent / second generation Grubbs catalyst / benzene / 0.5 h / Heating 4.1: 77 percent / p-toluenesulfonic acid / benzene / 4 h / Heating View Scheme

1: pyridinium chlorochromate / CH2Cl2 / Ambient temperature 2: H2NNH2*H2O, Na / ethane-1,2-diol; bis-(2-hydroxy-ethyl) ether / 185 °C View Scheme

1: NiCl2*6H2O, NaBH4 / methanol / Ambient temperature 2: i-Pr2NLi, HMPA / tetrahydrofuran / Ambient temperature 3: LiAlH4 / diethyl ether / Ambient temperature 4: pyridinium chlorochromate / CH2Cl2 / Ambient temperature 5: H2NNH2*H2O, Na / ethane-1,2-diol; bis-(2-hydroxy-ethyl) ether / 185 °C View Scheme

1: LiAlH4 / diethyl ether / Ambient temperature 2: pyridinium chlorochromate / CH2Cl2 / Ambient temperature 3: H2NNH2*H2O, Na / ethane-1,2-diol; bis-(2-hydroxy-ethyl) ether / 185 °C View Scheme

1: i-Pr2NLi, HMPA / tetrahydrofuran / Ambient temperature 2: LiAlH4 / diethyl ether / Ambient temperature 3: pyridinium chlorochromate / CH2Cl2 / Ambient temperature 4: H2NNH2*H2O, Na / ethane-1,2-diol; bis-(2-hydroxy-ethyl) ether / 185 °C View Scheme