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 / 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: 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: pyridine / 15 h / 20 °C 2: 0.5 N aq. HCl / tetrahydrofuran / -5 °C 3: 90 percent / SO3-pyridine complex, Et3N / dimethylsulfoxide / 0.25 h / 20 °C 4: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h 5: NaBH4 / methanol; tetrahydrofuran / -45 °C 6: K2CO3 / methanol / 1 h / 50 °C 7: p-toluenesulfonic acid / CH2Cl2 / 0.33 h / 25 °C 8: 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 9: 85 percent / 30percent H2O2 / ethyl acetate; methanol / 0.33 h / 40 °C 10: 71 percent / 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C View Scheme

1: 0.5 N aq. HCl / tetrahydrofuran / -5 °C 2: 90 percent / SO3-pyridine complex, Et3N / dimethylsulfoxide / 0.25 h / 20 °C 3: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h 4: NaBH4 / methanol; tetrahydrofuran / -45 °C 5: K2CO3 / methanol / 1 h / 50 °C 6: p-toluenesulfonic acid / CH2Cl2 / 0.33 h / 25 °C 7: 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 8: 85 percent / 30percent H2O2 / ethyl acetate; methanol / 0.33 h / 40 °C 9: 71 percent / 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C View Scheme

1: p-toluenesulfonic acid / CH2Cl2 / 0.33 h / 25 °C 2: 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 3: 85 percent / 30percent H2O2 / ethyl acetate; methanol / 0.33 h / 40 °C 4: 71 percent / 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C View Scheme

1: NaBH4 / methanol; tetrahydrofuran / -45 °C 2: K2CO3 / methanol / 1 h / 50 °C 3: p-toluenesulfonic acid / CH2Cl2 / 0.33 h / 25 °C 4: 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 5: 85 percent / 30percent H2O2 / ethyl acetate; methanol / 0.33 h / 40 °C 6: 71 percent / 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C View Scheme

1: K2CO3 / methanol / 1 h / 50 °C 2: p-toluenesulfonic acid / CH2Cl2 / 0.33 h / 25 °C 3: 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 4: 85 percent / 30percent H2O2 / ethyl acetate; methanol / 0.33 h / 40 °C 5: 71 percent / 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C View Scheme