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 View Scheme

1.1: LDA / tetrahydrofuran / 0.17 h / -78 °C 1.2: 69 percent / tetrahydrofuran / 0.5 h / -78 °C 2.1: 98 percent / t-BuOK / tetrahydrofuran / 0.67 h / 70 °C 3.1: EtMgBr / tetrahydrofuran / -78 - 20 °C 3.2: CuI / tetrahydrofuran / 0.17 h / 20 °C 3.3: 89 percent / tetrahydrofuran / 0.5 h / 20 °C 4.1: H2 / Pd(OH)2/C / methanol; ethyl acetate 5.1: cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.5 h / 0 °C 6.1: 4-(dimethylamino)pyridine; pyridine / 1 h / 20 °C View Scheme

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 View Scheme

1.1: 98 percent / t-BuOK / tetrahydrofuran / 0.67 h / 70 °C 2.1: EtMgBr / tetrahydrofuran / -78 - 20 °C 2.2: CuI / tetrahydrofuran / 0.17 h / 20 °C 2.3: 89 percent / tetrahydrofuran / 0.5 h / 20 °C 3.1: H2 / Pd(OH)2/C / methanol; ethyl acetate 4.1: cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.5 h / 0 °C 5.1: 4-(dimethylamino)pyridine; pyridine / 1 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 View Scheme

pyridine; 4-(N,N-dimethlyamino)pyridine T=20°C; 1 h;

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