1: 1) 60percent sodium hydride, 2) bromine / 1) DME, room temperature, 0.5 h, 2) room temperature, 1 h 2: 76 percent / acetic acid; dimethylformamide / 2 h / 80 °C 3: 1) 60percent sodium hydride / 1) DMF, 0 deg C, 0.5 h, 2) room temperature, 3 h 4: 100 percent / H2 / Raney Ni / acetic acid / 3 h 5: NaNO2, HOAc / acetic anhydride / 4 h / 0 °C 6: CCl4 / 5 h / Heating 7: 33.5 percent / 1 M H2SO4 / 1,2-dimethoxy-ethane / 24 h / 55 °C View Scheme

1: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight 2: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 3: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 4: CCl4 / Heating 5: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 6: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h 7: 41 percent / O2, cupric chloride, dimethylamine / dimethylformamide; H2O View Scheme

1: 85 percent / NaH, Br2 / 1,2-dimethoxy-ethane / Ambient temperature 2: Na2CO3 / dimethylformamide / 70 °C 3: NaH / dimethylformamide / Ambient temperature 5: 1.) LiOH; 2.) AcOH / 1.) EtOH, r.t.; 2.) r.t. 6: 80 percent / TFA / Ambient temperature 7: 73 percent / p-TsOH / toluene View Scheme

1: 85 percent / NaH, Br2 / 1,2-dimethoxy-ethane / Ambient temperature 2: Na2CO3 / dimethylformamide / 70 °C 3: NaH / dimethylformamide / Ambient temperature 5: 1.) LiOH; 2.) AcOH / 1.) EtOH, r.t.; 2.) r.t. 6: 80 percent / TFA / Ambient temperature View Scheme