1.1: 87 percent / NBS / CH2Cl2 / 1.83 h / -70 - -16 °C 2.1: t-BuLi / tetrahydrofuran; pentane / 0.07 h / -78 °C 2.2: tetrahydrofuran; pentane / 1.67 h / -78 - -10 °C 2.3: H2 / Pd(OH)2/C / methanol; ethyl acetate / 6 h / 20 °C / 750.08 Torr 3.1: NaIO4; RuCl3*xH2O / CCl4; acetonitrile; H2O / 2 h / 20 °C 3.2: tetrahydrofuran; methanol / 65 h / 20 °C View Scheme

1.1: 87 percent / NBS / CH2Cl2 / 1.83 h / -70 - -16 °C 2.1: t-BuLi / tetrahydrofuran; pentane / 0.07 h / -78 °C 2.2: tetrahydrofuran; pentane / 1.67 h / -78 - -10 °C 2.3: H2 / Pd(OH)2/C / methanol; ethyl acetate / 6 h / 20 °C / 750.08 Torr 3.1: NaIO4; RuCl3*xH2O / CCl4; acetonitrile; H2O / 2 h / 20 °C 3.2: tetrahydrofuran; methanol / 65 h / 20 °C View Scheme