1: 88 percent / dimethylformamide / 4 h 2: concd H2SO4, H2 / PtO2 / ethanol / 12 h / 2585.7 Torr 3: benzene / 3 h / Heating 4: 93 percent / LiAlH4 / tetrahydrofuran / 5 h / Heating View Scheme

2: 50 percent / lithium bis(trimethylsilyl)amide / -78 °C 3: H2 / 5percent platinum on carbon 4: H2O; dimethylsulfoxide / Heating; alkaline hydrolysis 5: boron tribromide View Scheme

1: 3 h / Heating 2: potassium t-butoxide / 1.) THF-HMPA, -60 deg C, 30 min; 2.) -20 deg C 5 min, rt overnight 3: 95 percent / p-toluenesulfonic acid / methanol / 2 h / Ambient temperature 4: hydrogen / Pt-C / ethyl acetate 5: 1.) DMSO; 2.) oxalyl chloride, triethylamine / 1.) CH2Cl2, -78 deg C, 5 min; 2.) CH2Cl, -78 deg C 5 min, rt 6: 1.) n-butyllithium / 1.) THF-hexane, 0 deg C 30 min; 2.) THF-hexane, -30 deg C 40 min, rt 7: 97 percent / NaOH / dimethylsulfoxide / 24 h / Heating 8: 67 percent / NaH, ethanethiol / dimethylformamide / 1.) 0 deg C, 30 min rt; 2.) reflux 3 h View Scheme

1: 88 percent / dimethylformamide / 4 h 2: concd H2SO4, H2 / PtO2 / ethanol / 12 h / 2585.7 Torr 3: benzene / 3 h / Heating 4: 93 percent / LiAlH4 / tetrahydrofuran / 5 h / Heating 5: 10 percent Spectr. / MnO2 / CH2Cl2 / 40 h / 23 °C View Scheme

1: 88 percent / dimethylformamide / 4 h 2: concd H2SO4, H2 / PtO2 / ethanol / 12 h / 2585.7 Torr 3: benzene / 3 h / Heating View Scheme

2: 50 percent / lithium bis(trimethylsilyl)amide / -78 °C 3: H2 / 5percent platinum on carbon 4: H2O; dimethylsulfoxide / Heating; alkaline hydrolysis View Scheme