1: 53 percent / NaH / tetrahydrofuran; dimethylformamide / 4 h / 20 °C 2: 78 percent / Pr4NRuO4; NMO; MS4A / acetonitrile 3: 92 percent / n-BuLi / tetrahydrofuran / 1 h / 20 °C 4: H2 / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C 5: 90 percent / PCC / CH2Cl2 / 2 h / 20 °C View Scheme

1: 78 percent / Pr4NRuO4; NMO; MS4A / acetonitrile 2: 92 percent / n-BuLi / tetrahydrofuran / 1 h / 20 °C 3: H2 / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C 4: 90 percent / PCC / CH2Cl2 / 2 h / 20 °C View Scheme

1: 92 percent / n-BuLi / tetrahydrofuran / 1 h / 20 °C 2: H2 / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C 3: 90 percent / PCC / CH2Cl2 / 2 h / 20 °C View Scheme

1: 92 percent / n-BuLi / tetrahydrofuran / 1 h / 20 °C 2: H2 / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C 3: 90 percent / PCC / CH2Cl2 / 2 h / 20 °C View Scheme

1: 81 percent / acetonitrile / 120 h / Heating 2: 92 percent / n-BuLi / tetrahydrofuran / 1 h / 20 °C 3: H2 / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C 4: 90 percent / PCC / CH2Cl2 / 2 h / 20 °C View Scheme

1: 98 percent / LiAlH4 / diethyl ether / 2 h 2: 100 percent Chromat. / PCC / CH2Cl2 / 24 h / 20 °C View Scheme

sodium hydride in tetrahydrofuran T=0 - 20°C; Reduction; Horner-Wadsworth-Emmons reaction; 4 h;