1: With ozone in dichloromethane T=-78°C; 2: With sodium tetrahydroborate in methanol T=0°C;

sodium tetrahydroborate in methanol T=-78 - 20°C;

1: With pyridine; ozone; solvent red 19 in ethanol; dichloromethane T=-70 - 65°C; 3 h; 2: With sodium tetrahydroborate in ethanol; dichloromethane; acetone T=20 - 35°C;

hydrogen; palladium on activated charcoal in ethyl acetate P=735.5 Torr;

1: With pyridine; ozone; solvent red 19 in dichloromethane T=-60 - -55°C; 0.5 h; 2: With sodium tetrahydroborate in ethanol; dichloromethane T=20°C; 1 h;

1: 93 percent / imidazole / CH2Cl2; dimethylformamide / 1.) RT, 15 h, 2.) 45 deg C, 20 h, 3.) 80 deg C, 6 h 2: 1.) ozone, 2.) NaBH4 / 1.) MeOH, pyridine, CH2Cl2, -78 deg C, 1 h, 2.) RT, 12 h 3: 95 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature View Scheme

potassium hydroxide in tetrahydrofuran; methanol; water T=25°C; 48 h; Yield given;

1: 96 percent / 10percent DMAP / pyridine / 3 h / 70 °C 2: 89 percent / H2 / Lindlar catalyst 3: 72 percent / BF3*Et2O 4: H2 / PtO2 5: KOH / tetrahydrofuran; methanol; H2O / 48 h / 25 °C View Scheme

2: diisobutylaluminium hydride 3: oxalic acid / tetrahydrofuran / Linde 4A molecular sieves 4: 82 percent / 1.) titanium tetrachloride, 2,4,6-trimethylpyridine, 2.) 1 M hydrochloric acid / CH2Cl2 / 1.) -78 degC, 5 min., 2.) -78 degC to r.t. 5: pyridinium chlorochromate / CH2Cl2 / 18 h / 25 °C 6: 7.5 M KOH / tetrahydrofuran; methanol; H2O / 48 h / 25 °C 7: 96 percent / 10percent DMAP / pyridine / 3 h / 70 °C 8: 89 percent / H2 / Lindlar catalyst 9: 72 percent / BF3*Et2O 10: H2 / PtO2 11: KOH / tetrahydrofuran; methanol; H2O / 48 h / 25 °C View Scheme

1: oxalic acid / tetrahydrofuran / Linde 4A molecular sieves 2: 82 percent / 1.) titanium tetrachloride, 2,4,6-trimethylpyridine, 2.) 1 M hydrochloric acid / CH2Cl2 / 1.) -78 degC, 5 min., 2.) -78 degC to r.t. 3: pyridinium chlorochromate / CH2Cl2 / 18 h / 25 °C 4: 7.5 M KOH / tetrahydrofuran; methanol; H2O / 48 h / 25 °C 5: 96 percent / 10percent DMAP / pyridine / 3 h / 70 °C 6: 89 percent / H2 / Lindlar catalyst 7: 72 percent / BF3*Et2O 8: H2 / PtO2 9: KOH / tetrahydrofuran; methanol; H2O / 48 h / 25 °C View Scheme