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

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 6: 86 percent / NaH / tetrahydrofuran / 4 h / 0 - 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 5: 86 percent / NaH / tetrahydrofuran / 4 h / 0 - 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 4: 86 percent / NaH / tetrahydrofuran / 4 h / 0 - 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 4: 86 percent / NaH / tetrahydrofuran / 4 h / 0 - 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 5: 86 percent / NaH / tetrahydrofuran / 4 h / 0 - 20 °C View Scheme

1: 1) Zn, Cl(1-) / 1) ether, 2) ether, 3 h, reflux 2: amalgamated zinc, HCl / ethanol / Heating 3: 1) lithium diisopropylamide / 1) THF, -78 deg C, 30 min 2) THF, -78 to 20 deg C 4: 1) NaIO4 / 1) MeOH, H2O, 24 h, RT 2) toluene, 14 h, 120 deg C View Scheme

1: amalgamated zinc, HCl / ethanol / Heating 2: 1) lithium diisopropylamide / 1) THF, -78 deg C, 30 min 2) THF, -78 to 20 deg C 3: 1) NaIO4 / 1) MeOH, H2O, 24 h, RT 2) toluene, 14 h, 120 deg C View Scheme

sodium periodate 1) MeOH, H2O, 24 h, RT 2) toluene, 14 h, 120 deg C; Yield given. Multistep reaction;

1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 30 min 2) THF, -78 to 20 deg C 2: 1) NaIO4 / 1) MeOH, H2O, 24 h, RT 2) toluene, 14 h, 120 deg C View Scheme