acetic acid 14 h;

1: 95 percent / p-toluenesulfonic acid / CH2Cl2 / 0.5 h 2: 79 percent / diisobutylaluminum hydride / toluene; hexane / 0.33 h 3: 1.) sodium methylsulfinylcarbanide / 1.) Me2SO, 2.) Me2SO, 2 h 4: Jones reagent / acetone / 0.08 h / -20 °C 5: 43 percent / 65percent aq. acetic acid / 14 h View Scheme

1: 1.) sodium methylsulfinylcarbanide / 1.) Me2SO, 2.) Me2SO, 2 h 2: Jones reagent / acetone / 0.08 h / -20 °C 3: 43 percent / 65percent aq. acetic acid / 14 h View Scheme

1: 79 percent / diisobutylaluminum hydride / toluene; hexane / 0.33 h 2: 1.) sodium methylsulfinylcarbanide / 1.) Me2SO, 2.) Me2SO, 2 h 3: Jones reagent / acetone / 0.08 h / -20 °C 4: 43 percent / 65percent aq. acetic acid / 14 h View Scheme

1: Jones reagent / acetone / 0.08 h / -20 °C 2: 43 percent / 65percent aq. acetic acid / 14 h View Scheme

1: 90 percent / 1 h / 145 °C 2: CrO3/pyridine, activated silica gel / CH2Cl2 / 0.42 h 3: KOH / CH2Cl2 / 0.33 h / Ambient temperature 4: 1 N hydrochloric acid / acetone / 0.17 h / 20 °C 5: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 6: 85 percent / pyridine / 2 h / 5 °C 7: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C 8: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min 9: 90 percent / acetone / 1.5 h / -45 °C 10: CrO3/pyridine / CH2Cl2 11: aq. acetic acid / methanol / 0.08 h View Scheme

1: K2CO3 / 5 h / 20 °C 2: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 3: 85 percent / pyridine / 2 h / 5 °C 4: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C 5: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min 6: 90 percent / acetone / 1.5 h / -45 °C 7: CrO3/pyridine / CH2Cl2 8: aq. acetic acid / methanol / 0.08 h View Scheme

1: KOH / CH2Cl2 / 0.33 h / Ambient temperature 2: 1 N hydrochloric acid / acetone / 0.17 h / 20 °C 3: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 4: 85 percent / pyridine / 2 h / 5 °C 5: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C 6: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min 7: 90 percent / acetone / 1.5 h / -45 °C 8: CrO3/pyridine / CH2Cl2 9: aq. acetic acid / methanol / 0.08 h View Scheme

1: CrO3/pyridine, activated silica gel / CH2Cl2 / 0.42 h 2: KOH / CH2Cl2 / 0.33 h / Ambient temperature 3: 1 N hydrochloric acid / acetone / 0.17 h / 20 °C 4: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 5: 85 percent / pyridine / 2 h / 5 °C 6: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C 7: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min 8: 90 percent / acetone / 1.5 h / -45 °C 9: CrO3/pyridine / CH2Cl2 10: aq. acetic acid / methanol / 0.08 h View Scheme

1: 90 percent / aluminum diisobutyl-4-methyl-2,6-di-tert-butylphenoxide / CH2Cl2 / 0.5 h / -78 °C 2: 85 percent / pyridine / 2 h / 5 °C 3: 0.24 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C 4: 2.) 1 N hydrochloric acid / 1.) benzene, 20 deg C, 3 h, 2.) 10 min 5: 90 percent / acetone / 1.5 h / -45 °C 6: CrO3/pyridine / CH2Cl2 7: aq. acetic acid / methanol / 0.08 h View Scheme