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

1.1: NaH / tetrahydrofuran / 0.08 h / 20 °C 1.2: tetrahydrofuran / 1 h 2.1: LiAlH4; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C 3.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C 4.1: 1.0 M aq. NaOH / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme

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

1: 81 percent / sodium hydride / tetrahydrofuran / 1 h / Ambient temperature 2: 92 percent / 65percent aq. acetic acid / tetrahydrofuran / 1.5 h / 40 °C 3: diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / toluene / 1.) -78 deg C, 15 min; 2.) -20 deg C, 2 h 4: Et3N / p-toluenesulfonic acid / CH2Cl2 / 0.17 h / Ambient temperature 5: K2CO3 / methanol / 1 h / 45 °C 6: triphenylphosphine, diethyl azodicarboxylate / benzene / 2 h / Ambient temperature 7: p-toluenesulfonic acid, Et3N / methanol / 1 h / Ambient temperature 8: NaN3, dimethylsulfoxide / 19 h / 45 °C 9: toluene / 20 h / 70 °C View Scheme

1: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h 2: 36 percent / NaBH4 / methanol; tetrahydrofuran / -45 °C 3: K2CO3 / methanol / 1 h / 50 °C 4: p-toluenesulfonic acid / CH2Cl2 / 0.33 h / 25 °C 5: 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