1: 81 percent / 35percent aq. H2O2 / tetrahydrofuran / 1.) -5 deg C, 1 h; 2.) rt, 1.5 h 2: 87 percent / C5H5NHBr3 / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) rt, 2.5 h 3: 72 percent / NaNH2 / liquid ammonia; diethyl ether / 1.) -50 deg C, 30 min; 2.) -27 deg C, 3.5 h 4: 1) n-BuLi / 1) hexane, THF, -5 deg C, 45 min; 2) THF, -60 deg C, 1 h, then room temp. 5: 1) NaOH / 1) MeOH, room temp., 30 min; 2) MeOH, room temp., 4 h 6: 1) CuI / 1) THF, -65 deg C, 15 min; 2) THF, -65 deg C, 3 h 7: 90 percent / LiAlH4 / diethyl ether / 3 h / 0 °C View Scheme

1: 1) CuI / 1) THF, -65 deg C, 15 min; 2) THF, -65 deg C, 3 h 2: 90 percent / LiAlH4 / diethyl ether / 3 h / 0 °C View Scheme

1: 1.) NaH / 1.) mineral oil, hexan, THF, room temperature, 2 h, 2.) mineral oil, hexan, THF, room temperature, 16 h 2: 91 percent / DIBAH / hexane / 1 h / -10 °C View Scheme

1: 81 percent / pyridine / 24 h / 0 °C 2: 95 percent / LiBr / 1,2-dimethoxy-ethane / 15 h / 50 °C 3: 1.) Mg, 1,2-dibromomethane, 2.) CuI, pyrrolidine / 1.) Et2O, 2.5 h, 2.) Et2O, 15 min, room temperature, 3.) Et2O, -90 deg C, 3 h 4: 95 percent / DIBAH / diethyl ether; hexane / 2 h / Ambient temperature View Scheme

1: 1.) Mg, 1,2-dibromomethane, 2.) CuI, pyrrolidine / 1.) Et2O, 2.5 h, 2.) Et2O, 15 min, room temperature, 3.) Et2O, -90 deg C, 3 h 2: 95 percent / DIBAH / diethyl ether; hexane / 2 h / Ambient temperature View Scheme

1: 95 percent / LiBr / 1,2-dimethoxy-ethane / 15 h / 50 °C 2: 1.) Mg, 1,2-dibromomethane, 2.) CuI, pyrrolidine / 1.) Et2O, 2.5 h, 2.) Et2O, 15 min, room temperature, 3.) Et2O, -90 deg C, 3 h 3: 95 percent / DIBAH / diethyl ether; hexane / 2 h / Ambient temperature View Scheme