1: 71 percent / anhydrous sodium acetate, Br2 / acetic acid / 1.) 80 deg C, 6 h, 2.) 25 deg C, 16 h; 2: 1.) n-butyllithium / 1.) ether, hexane, -70 deg C, 10 min, 2.) -55 to -70 deg C, 15 min; View Scheme

n-butyllithium 1.) ether, hexane, -70 deg C, 10 min, 2.) -55 to -70 deg C, 15 min;; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

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: 64 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 1.) -30 to -20 deg C, 10 min, 2.) heating from -30 to -5 deg C, 2 h; 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; 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.) -95 deg C; 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 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 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: 80 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 1 h / 25 °C 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, 2.) methanol / 1.) toluene, ether, pentan, -100 deg C, 20 min. 2.) -85 deg C; 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