1: With potassium hydroxide in water 1 h; Reflux; 2: With hydrogenchloride in water pH=2;

sodium hydroxide; hydrogen; acetic acid; (S,S)-tartaric acid modified Raney nickel ((S,S)-TA-NaBr-MRNi-U) 1.) C2H5COOCH3, 100 deg C, 100 kg/cm2; Yield given. Multistep reaction;

lithium hydroxide in tetrahydrofuran; methanol; water Hydrolysis;

1: hydrogen; RuCl2[(S)-BINAP]; HCl / methanol / 3800.26 - 4560.31 Torr 2: LiOH / tetrahydrofuran; methanol; H2O View Scheme

1: pyridine / CH2Cl2 / 1 h / Ambient temperature 2: methanol / 5 h / Heating 3: 1.) H2, AcOH, 2.) NaOH / 1.) (S,S)-tartaric acid-NaBr-Raney nickel ((S,S)-TA-NaBr-MRNi) / 1.) C2H5COOCH3, 100 deg C, 100 kg/cm2 View Scheme

1: methanol / 5 h / Heating 2: 1.) H2, AcOH, 2.) NaOH / 1.) (S,S)-tartaric acid-NaBr-Raney nickel ((S,S)-TA-NaBr-MRNi) / 1.) C2H5COOCH3, 100 deg C, 100 kg/cm2 View Scheme

sodium hydroxide 16 h; Ambient temperature;

1: lipase(Amano PS) / tetrahydrofuran 2: 6M HCl / methanol / 40 °C 3: NaOH / methanol / Heating View Scheme

1: HCl / methanol; H2O / 48 h / 40 °C 2: 11.6 g / NaOH / methanol; H2O / 0.5 h / 90 °C View Scheme

1: 1.) Mg, 2.) CuI / 1.) THF, 1 h, 2.) 0 deg C, 80 min 2: aq. HOAc / tetrahydrofuran / 1.5 h 3: 60 percent / pyridine / tetrahydrofuran / 1.) -30 deg C, 1 h, 2.) 0 deg C, 16 h 4: LiBr / acetone / 2 h / Heating 5: tetrahydrofuran / Heating 6: LDA / tetrahydrofuran / -78 °C 7: Li(sec-Bu)3BH / tetrahydrofuran / -10 °C 8: hexamethylphosphoric acid triamide / 1 h / 110 °C 9: Bu3SnH, AIBN / toluene / 1 h / 60 °C View Scheme