potassium peroxomonosulphate in tetrahydrofuran; methanol; water T=30°C; 3 h;

potassium in tetrahydrofuran; methanol; water; toluene

diisobutylaluminium hydride; acetic acid in dichloromethane; water; dimethyl sulfoxide; toluene

1: 71 percent / NaOAc, Br2 / acetic acid / 1.) 80 deg C, 6 h, 2.) 25 deg C, 16 h 2: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 3: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 4: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 5: 1.) t-BuLi / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, from -100 deg C to 0 deg C 6: 49.5percent KHSO5 / tetrahydrofuran; methanol; H2O / 1 h / 30 °C View Scheme

1: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 2: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 3: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 4: 1.) t-BuLi / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, from -100 deg C to 0 deg C 5: 49.5percent KHSO5 / tetrahydrofuran; methanol; H2O / 1 h / 30 °C View Scheme

1: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 2: 1.) t-BuLi / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, from -100 deg C to 0 deg C 3: 49.5percent KHSO5 / tetrahydrofuran; methanol; H2O / 1 h / 30 °C View Scheme

1: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 2: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 3: 1.) t-BuLi / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, from -100 deg C to 0 deg C 4: 49.5percent KHSO5 / tetrahydrofuran; methanol; H2O / 1 h / 30 °C View Scheme

1: 1.) t-BuLi / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, from -100 deg C to 0 deg C 2: 49.5percent KHSO5 / tetrahydrofuran; methanol; H2O / 1 h / 30 °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

1: 1.) potassium iodate, aq. H2SO4, 2.) potassium iodide; / 1.) 90-100 deg C, 30 min, 2.) water, 1.5 h; 2: 79 percent / phosphorus oxychloride / 4 h / Heating 3: 53 percent / N,N-diisopropylethylamine, tri-o-tolylphosphine / palladium acetate / dimethylformamide / 1.) 100 deg C, 20 min, 2.) 116 deg C, 20 min; 4: 0.36 g / diisobutylaluminium hydride / CH2Cl2; toluene / 0.08 h / -65 °C 5: NaH / dimethylsulfoxide / 0.25 h View Scheme