1: 90 percent / SO3-pyridine complex, Et3N / dimethylsulfoxide / 0.25 h / 20 °C 2: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h 3: NaBH4 / methanol; tetrahydrofuran / -45 °C 4: K2CO3 / methanol / 1 h / 50 °C 5: p-toluenesulfonic acid / CH2Cl2 / 0.33 h / 25 °C 6: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 20 deg C, 30 min 7: 85 percent / 30percent H2O2 / ethyl acetate; methanol / 0.33 h / 40 °C 8: 71 percent / 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C View Scheme

1.1: PCC; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C 2.1: NaH / tetrahydrofuran / 0.08 h / 20 °C 2.2: tetrahydrofuran / 1 h 3.1: LiAlH4; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C 4.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C 5.1: 1.0 M aq. NaOH / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme

1: PCC, 4 Angstroem molecular sieves, NaOAc / CH2Cl2 / 0 °C 2: NaH / tetrahydrofuran / Ambient temperature 3: 92 percent / (S)-binaphthol, LiAlH4 / ethanol; tetrahydrofuran / -100 - -78 °C 4: 93 percent / acetic acid / H2O; tetrahydrofuran / 40 °C 5: 95 percent / 1N NaOH / methanol; tetrahydrofuran / Ambient temperature View Scheme

1: 90 percent / SO3-pyridine complex, Et3N / dimethylsulfoxide / 0.25 h / 20 °C 2: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h 3: 36 percent / NaBH4 / methanol; tetrahydrofuran / -45 °C 4: K2CO3 / methanol / 1 h / 50 °C 5: p-toluenesulfonic acid / CH2Cl2 / 0.33 h / 25 °C 6: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 20 deg C, 30 min View Scheme