1: sodium hydroxide; water / ethanol / 16 h / 20 °C 2: water; acetone / 23 h / 10 - 50 °C 3: hydrogenchloride / water; tert-butyl methyl ether / 1 h / 20 °C / pH 1 View Scheme

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 18 h / 20 - 120 °C 2: sodium hydroxide; water / ethanol / 16 h / 20 °C 3: water; acetone / 23 h / 10 - 50 °C 4: hydrogenchloride / water; tert-butyl methyl ether / 1 h / 20 °C / pH 1 View Scheme

phosphate buffer; porcine pancreatic lipase T=20°C; pH=7.00; 12 h; Enzymatic reaction; Title compound not separated from byproducts;

lithium hydroxide; titanium tetrachloride 1.) CH2Cl2, petroeum ether, -20 deg C, 7 days, 2.) THF, water, room temperature, 10 h; Yield given. Multistep reaction;

jones' reagent

jones' reagent Yield given. Yields of byproduct given;

lithium hydroxide; ethylaluminum dichloride 1.) CH2Cl2, -78 deg C, 2.) THF, H2O, room temp.; ee.: 93percent; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1: 1.) iodine, potassium iodide, NaHCO3, 2.) DIBALH / 1.) CH2Cl2, H2O, 0 deg C, 1.5 h, 2.) THF, hexane, -78 deg C, 0.5 h 2: 92 percent / NaH / dimethylformamide / 0.25 h / 0 °C 3: 98 percent / NaBH4 / ethanol / 1 h / Ambient temperature 4: 90 percent / H2O2 / tetrahydrofuran / 0 deg C, 0.5 h, room temperature, 5 h 5: 88 percent / tetrahydrofuran / 0.5 h / Heating View Scheme