1: 1.) n-BuLi / 1.) -78 deg C, THF/hexane, 5 min, 2.) -78 deg C, 10 min; 25 deg C 2: 65 percent / 2N H2SO4 / tetrahydrofuran / Ambient temperature View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 1.2: tetrahydrofuran; hexane / 0.17 h / -78 °C 2.1: 3.57 g / bromine / CH2Cl2 / 0.17 h / -78 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C 1.2: HMPA / tetrahydrofuran; hexane / -78 - -15 °C 2.1: 3.20 g / bromine / CH2Cl2 / 0.17 h / -78 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 1.2: tetrahydrofuran; hexane / 0.17 h / -78 °C 2.1: 3.57 g / bromine / CH2Cl2 / 0.17 h / -78 °C 3.1: 76 percent / NaBH4 / ethanol / 3 h / 20 °C 4.1: 81 percent / DCC; DMAP / CH2Cl2 5.1: 6 percent / HMPA; tert-butyldimethylsilyl chloride; LHMDS / tetrahydrofuran / 1.33 h / -78 - 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 1.2: tetrahydrofuran; hexane / 0.17 h / -78 °C 2.1: 3.57 g / bromine / CH2Cl2 / 0.17 h / -78 °C 3.1: 76 percent / NaBH4 / ethanol / 3 h / 20 °C 4.1: 81 percent / DCC; DMAP / CH2Cl2 5.1: 6 percent / HMPA; tert-butyldimethylsilyl chloride; LHMDS / tetrahydrofuran / 1.33 h / -78 - 20 °C 6.1: 72 percent / HMPA; tert-butyldimethylsilyl chloride; LHMDS / tetrahydrofuran / 1.33 h / -78 - 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 1.2: tetrahydrofuran; hexane / 0.17 h / -78 °C 2.1: 3.57 g / bromine / CH2Cl2 / 0.17 h / -78 °C 3.1: 76 percent / NaBH4 / ethanol / 3 h / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 1.2: tetrahydrofuran; hexane / 0.17 h / -78 °C 2.1: 3.57 g / bromine / CH2Cl2 / 0.17 h / -78 °C 3.1: 76 percent / NaBH4 / ethanol / 3 h / 20 °C 4.1: 84 percent / DMAP; pyridine / CH2Cl2 / 3 h / cooling View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 1.2: tetrahydrofuran; hexane / 0.17 h / -78 °C 2.1: 3.57 g / bromine / CH2Cl2 / 0.17 h / -78 °C 3.1: 76 percent / NaBH4 / ethanol / 3 h / 20 °C 4.1: 84 percent / DMAP; pyridine / CH2Cl2 / 3 h / cooling 5.1: 74 percent / HMPA; tert-butyldimethylsilyl chloride; LHMDS / tetrahydrofuran / 1.33 h / -78 - 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 1.2: tetrahydrofuran; hexane / 0.17 h / -78 °C 2.1: 3.57 g / bromine / CH2Cl2 / 0.17 h / -78 °C 3.1: 76 percent / NaBH4 / ethanol / 3 h / 20 °C 4.1: 76 percent / DCC; DMAP / CH2Cl2 5.1: 94 percent / HMPA; tert-butyldimethylsilyl chloride; LHMDS / tetrahydrofuran / 1.33 h / -78 - 20 °C 6.1: 90 percent / DBU / tetrahydrofuran / 1 h / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 1.2: tetrahydrofuran; hexane / 0.17 h / -78 °C 2.1: 3.57 g / bromine / CH2Cl2 / 0.17 h / -78 °C 3.1: 76 percent / NaBH4 / ethanol / 3 h / 20 °C 4.1: 78 percent / DCC; DMAP / CH2Cl2 5.1: HMPA; tert-butyldimethylsilyl chloride; LHMDS / tetrahydrofuran / 1.58 h / -78 - 20 °C 5.2: 83 percent / aq. HCl / tetrahydrofuran / 0.33 h 6.1: 91 percent / DBU / tetrahydrofuran / 1 h / 20 °C 7.1: 76 percent / K2CO3; MeOH / 20 °C View Scheme