sulfuric acid; hydrogen; palladium on activated charcoal in ethanol 36 h;

boron tribromide in dichloromethane T=-78 - 20°C; 0.75 h;

1: 82 percent / H2 / 5percent Pd/C / pentane / 5 °C 2: 93 percent / KO-t-Bu / 2-methyl-propan-2-ol / 8 h / 45 °C 3: 75 percent / DDQ / 0.08 h 4: 1.) NaH / 1.) Me2SO, 15 min 5: H2 / 30percent Pd/C / ethyl acetate; pyridine / 3 h 6: 1.) TsOH*H2O, 2.) PyHBr3 / 1.) AcOH, reflux, 80 min, 2.) 30 min 7: 80 percent / H2, conc, H2SO4 / 10percent Pd/C / ethanol / 36 h View Scheme

1: 93 percent / KO-t-Bu / 2-methyl-propan-2-ol / 8 h / 45 °C 2: 75 percent / DDQ / 0.08 h 3: 1.) NaH / 1.) Me2SO, 15 min 4: H2 / 30percent Pd/C / ethyl acetate; pyridine / 3 h 5: 1.) TsOH*H2O, 2.) PyHBr3 / 1.) AcOH, reflux, 80 min, 2.) 30 min 6: 80 percent / H2, conc, H2SO4 / 10percent Pd/C / ethanol / 36 h View Scheme

1: 1.) NaH / 1.) Me2SO, 15 min 2: H2 / 30percent Pd/C / ethyl acetate; pyridine / 3 h 3: 1.) TsOH*H2O, 2.) PyHBr3 / 1.) AcOH, reflux, 80 min, 2.) 30 min 4: 80 percent / H2, conc, H2SO4 / 10percent Pd/C / ethanol / 36 h View Scheme

1: 75 percent / DDQ / 0.08 h 2: 1.) NaH / 1.) Me2SO, 15 min 3: H2 / 30percent Pd/C / ethyl acetate; pyridine / 3 h 4: 1.) TsOH*H2O, 2.) PyHBr3 / 1.) AcOH, reflux, 80 min, 2.) 30 min 5: 80 percent / H2, conc, H2SO4 / 10percent Pd/C / ethanol / 36 h View Scheme

1: 1.) TsOH*H2O, 2.) PyHBr3 / 1.) AcOH, reflux, 80 min, 2.) 30 min 2: 80 percent / H2, conc, H2SO4 / 10percent Pd/C / ethanol / 36 h View Scheme

1: H2 / 30percent Pd/C / ethyl acetate; pyridine / 3 h 2: 1.) TsOH*H2O, 2.) PyHBr3 / 1.) AcOH, reflux, 80 min, 2.) 30 min 3: 80 percent / H2, conc, H2SO4 / 10percent Pd/C / ethanol / 36 h View Scheme

1: With pyridine; thionyl chloride T=0°C; 0.166667 h; 2: With potassium tert-butylate in o-xylene T=160°C; Dieckmann condensation; 0.0833333 h; 3: With magnesium chloride in dimethyl sulfoxide T=160°C; 3 h;

potassium hydroxide in methanol; water 90 h; Heating;