1: 68 percent / 1.) Br / 2.) THF, 2.) 25 deg C, 30 min 2: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C 3: pyridine; diethyl ether / 6 h / Heating 4: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 5: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 6: 77 percent / H2SO4 conc. / 4 h / Heating 7: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 8: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 9: diethyl ether / 0.5 h / 0 °C 10: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme

1: pyridine; diethyl ether / 6 h / Heating 2: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 3: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 4: 77 percent / H2SO4 conc. / 4 h / Heating 5: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 6: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 7: diethyl ether / 0.5 h / 0 °C 8: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme

1: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 2: 77 percent / H2SO4 conc. / 4 h / Heating 3: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 4: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 5: diethyl ether / 0.5 h / 0 °C 6: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme

1: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C 2: pyridine; diethyl ether / 6 h / Heating 3: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 4: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 5: 77 percent / H2SO4 conc. / 4 h / Heating 6: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 7: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 8: diethyl ether / 0.5 h / 0 °C 9: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme

1: 77 percent / H2SO4 conc. / 4 h / Heating 2: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 3: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 4: diethyl ether / 0.5 h / 0 °C 5: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme

1: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 2: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 3: diethyl ether / 0.5 h / 0 °C 4: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme

1: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 2: diethyl ether / 0.5 h / 0 °C 3: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme

2: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C 3: 63 percent / p-toluenesulfonic acid / 6 h / Heating 4: 1.) copper(I) iodide / 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h View Scheme

1: diethyl ether / 0.5 h / 0 °C 2: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme

tetra(n-butyl)ammonium hydroxide in benzene other reagents; Yield given. Yields of byproduct given. Title compound not separated from byproducts;