1: 69 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O / 20 °C 2: NaOBr, NaOH / dioxane; H2O / 4 h / 0 °C 3: 83 percent / LiAlH4 / diethyl ether / 2 h / Heating View Scheme

1: 69 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O / 20 °C 2: NaOBr, NaOH / dioxane; H2O / 4 h / 0 °C 3: 83 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 98 percent / 4-dimethylaminopyridine / 2 h / 100 °C View Scheme

1: 69 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O / 20 °C 2: NaOBr, NaOH / dioxane; H2O / 4 h / 0 °C View Scheme

dilithium tetrachlorocuprate in tetrahydrofuran

1: 1.) 0.75M 9-borabicyclo<3.3.1>nonane; 2.) 3N NaOH, 26percent H2O2 / 1.) THF, 0 deg C, 2-3 h; 2.) 20 deg C, 2-3 h 2: PBr3 / 1.) pyridine, hexane, 3-5 deg C, 3h; 2.) 20 deg C, 12 h 3: 1.) Mg / 1.) ether; 2.) ether; HCl 4: 89 percent / LiAlH4 / diethyl ether View Scheme

1: 1.) 0.75M 9-borabicyclo<3.3.1>nonane; 2.) 3N NaOH, 26percent H2O2 / 1.) THF, 0 deg C, 2-3 h; 2.) 20 deg C, 2-3 h 2: PBr3 / 1.) pyridine, hexane, 3-5 deg C, 3h; 2.) 20 deg C, 12 h 3: 1.) Mg / 2.) Li2CuCl4 / 1.) THF; 2.) 0 deg C, 3 h, 20 deg C, 1 h 4: 89 percent / potassium iodide / acetic acid / 24 h / Heating View Scheme