sodium tungstate; dihydrogen peroxide in tetrahydrofuran; water T=20°C; 0.5 h;

diisobutylaluminium hydride in toluene T=0°C; Reduction; 0.333333 h;

1.1: NaH / 1,2-dimethoxy-ethane / 0.25 h / 0 °C 1.2: 1,2-dimethoxy-ethane / 0.25 h / 0 °C 2.1: DIBAL / toluene / 0.33 h / 0 °C View Scheme

1.1: magnesium / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 1.2: 0 - 20 °C 2.1: sulfuric acid / tetrahydrofuran; water / 10 h / Reflux 3.1: sodium tungstate; dihydrogen peroxide / tetrahydrofuran; water / 0.5 h / 20 °C View Scheme

1: sulfuric acid / tetrahydrofuran; water / 10 h / Reflux 2: sodium tungstate; dihydrogen peroxide / tetrahydrofuran; water / 0.5 h / 20 °C View Scheme

sodium tetrahydroborate; thionyl chloride 1) reflux, 1 h; 2) CH2Cl2, EtOH, 10 deg C, 1 h; Yield given. Multistep reaction;

1: 82 percent / 4 Anstroem molecular sieves, diisopropyl L-tartrate, Ti(OPr-i)4, t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / 4 h / -20 °C 2: 1.) NaH, 2.) ZnCl2, 3.) 4 Angstroem molecular sieves / 1) THF, 5 deg C, 30 min; 2) THF, 5 deg C, 30 min; 3) THF, 55 deg C, 16 h 3: 1.) Et3N, MeSO2Cl, 2.) aq. NaOH / 1) pyridine, 5 deg C, 2 h; 2) pyridine, pH 12.5 4: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C 5: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5 View Scheme