sodium periodate; ruthenium trichloride in tetrachloromethane; water; acetonitrile T=20°C; 48 h;

1.1: EtMgBr / tetrahydrofuran / -78 - 20 °C 1.2: CuI / tetrahydrofuran / 0.17 h / 20 °C 1.3: 89 percent / tetrahydrofuran / 0.5 h / 20 °C 2.1: H2 / Pd(OH)2/C / methanol; ethyl acetate 3.1: cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.5 h / 0 °C 4.1: 4-(dimethylamino)pyridine; pyridine / 1 h / 20 °C 5.1: 37 percent / NaIO4 / RuCl3*H2O / CCl4; acetonitrile; H2O / 48 h / 20 °C View Scheme

1: H2 / Pd(OH)2/C / methanol; ethyl acetate 2: cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.5 h / 0 °C 3: 4-(dimethylamino)pyridine; pyridine / 1 h / 20 °C 4: 37 percent / NaIO4 / RuCl3*H2O / CCl4; acetonitrile; H2O / 48 h / 20 °C View Scheme