1: 53 percent / N,N-diisopropylethylamine, tri-o-tolylphosphine / palladium acetate / dimethylformamide / 1.) 100 deg C, 20 min, 2.) 116 deg C, 20 min; 2: 0.36 g / diisobutylaluminium hydride / CH2Cl2; toluene / 0.08 h / -65 °C 3: NaH / dimethylsulfoxide / 0.25 h View Scheme

1: 34 percent / NaHCO3 / palladium acetate / dimethylformamide / 6 h / 120 °C 2: NaBH4 / ethanol; tetrahydrofuran 3: aq. 48percent HBr / acetic acid View Scheme

1: 79 percent / phosphorus oxychloride / 4 h / Heating 2: 53 percent / N,N-diisopropylethylamine, tri-o-tolylphosphine / palladium acetate / dimethylformamide / 1.) 100 deg C, 20 min, 2.) 116 deg C, 20 min; 3: 0.36 g / diisobutylaluminium hydride / CH2Cl2; toluene / 0.08 h / -65 °C 4: NaH / dimethylsulfoxide / 0.25 h View Scheme

1: NaBH4 / ethanol; tetrahydrofuran / 1 h 2: aq. 48percent HBr / acetic acid / 0.5 h / 85 °C 3: 59 percent / H2 / W-2 Raney Nickel / ethanol; tetrahydrofuran / 6 h 4: 1.) t-butyllithium / 1.) toluene, ether, pentan, -100 deg C, 20 min. 2.) 0 deg C; 5: 73 percent / potassium persulfate / methanol; tetrahydrofuran; H2O / 3 h / 30 °C View Scheme

1: aq. 48percent HBr / acetic acid / 0.5 h / 85 °C 2: 59 percent / H2 / W-2 Raney Nickel / ethanol; tetrahydrofuran / 6 h 3: 1.) t-butyllithium / 1.) toluene, ether, pentan, -100 deg C, 20 min. 2.) 0 deg C; 4: 73 percent / potassium persulfate / methanol; tetrahydrofuran; H2O / 3 h / 30 °C View Scheme

1: 34 percent / anhydrous sodium acetate, Br2 / acetic acid / 1.) 80 deg C, 6 h, 2.) 23 deg C, 64 h; 2: 34 percent / NaHCO3 / palladium acetate / dimethylformamide / 6 h / 120 °C 3: NaBH4 / ethanol; tetrahydrofuran 4: aq. 48percent HBr / acetic acid View Scheme

1: 76 percent / aq. KOH / methanol; tetrahydrofuran / exothermic reaction 2: NaBH4 / ethanol; tetrahydrofuran / 1 h 3: aq. 48percent HBr / acetic acid / 0.5 h / 85 °C 4: 59 percent / H2 / W-2 Raney Nickel / ethanol; tetrahydrofuran / 6 h 5: 1.) t-butyllithium / 1.) toluene, ether, pentan, -100 deg C, 20 min. 2.) 0 deg C; 6: 73 percent / potassium persulfate / methanol; tetrahydrofuran; H2O / 3 h / 30 °C View Scheme