hydrogen; palladium on activated charcoal in ethanol T=20°C; 20 h;

1.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.25 h / -70 °C 1.2: 47 percent / toluene; tetrahydrofuran / 0.5 h / -70 °C 2.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.5 h / -70 °C 2.2: 13 percent / oxodiperoxymolybdenum(pyridine)(HMPTA) / toluene; tetrahydrofuran / 2 h / -70 °C 3.1: 86 percent / H2 / Pd-C / ethyl acetate / 2 h / 20 °C View Scheme

1.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.25 h / -70 °C 1.2: 47 percent / toluene; tetrahydrofuran / 0.5 h / -70 °C 2.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.5 h / -70 °C 2.2: 13 percent / oxodiperoxymolybdenum(pyridine)(HMPTA) / toluene; tetrahydrofuran / 2 h / -70 °C 3.1: 86 percent / H2 / Pd-C / ethyl acetate / 2 h / 20 °C View Scheme

1.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.5 h / -70 °C 1.2: 13 percent / oxodiperoxymolybdenum(pyridine)(HMPTA) / toluene; tetrahydrofuran / 2 h / -70 °C 2.1: 86 percent / H2 / Pd-C / ethyl acetate / 2 h / 20 °C View Scheme

1.1: 70 percent / p-TsOH / benzene / Heating 2.1: 71 percent / LHMDS / tetrahydrofuran / 5 h / -75 °C 3.1: BH3*Me2S / diethyl ether / 5 h / Heating 3.2: 88 percent / aq. HCl / diethyl ether / 3 h / Heating 4.1: 98 percent / H2 / Pd/C / ethanol / 20 h / 20 °C View Scheme

1.1: 87 percent / KOH / ethanol / 72 h / 20 °C 2.1: 70 percent / p-TsOH / benzene / Heating 3.1: 71 percent / LHMDS / tetrahydrofuran / 5 h / -75 °C 4.1: BH3*Me2S / diethyl ether / 5 h / Heating 4.2: 88 percent / aq. HCl / diethyl ether / 3 h / Heating 5.1: 98 percent / H2 / Pd/C / ethanol / 20 h / 20 °C View Scheme

1.1: 71 percent / LHMDS / tetrahydrofuran / 5 h / -75 °C 2.1: BH3*Me2S / diethyl ether / 5 h / Heating 2.2: 88 percent / aq. HCl / diethyl ether / 3 h / Heating 3.1: 98 percent / H2 / Pd/C / ethanol / 20 h / 20 °C View Scheme

1.1: BH3*Me2S / diethyl ether / 5 h / Heating 1.2: 88 percent / aq. HCl / diethyl ether / 3 h / Heating 2.1: 98 percent / H2 / Pd/C / ethanol / 20 h / 20 °C View Scheme