1: aq. NaOH / dioxane / 0.75 h / Heating 2: H2 / Pd/C / methanol View Scheme

1: 76 percent / AcONa / 8 h / 190 - 195 °C 2: 89 percent / H2 / 5 percent Pd/C / methanol / 1.5 h View Scheme

1: aq. KOH 2: Na-Hg, aq. NaOH View Scheme

1: LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: aq. KOH / ethanol / 3 h / Heating 5: 1.) LDA / 1.) hexane, THF, -70 deg C, 1.5 h, 2.) hexane, THF, from -70 deg C to RT 6: 55 percent / P2O5, MeSO3H / 1 h / Ambient temperature 7: 90 percent / pyridine hydrochloride / 0.5 h / 210 °C 8: 68 percent / K2CO3 / acetone; dimethylformamide / 18 h / Heating 9: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 10: conc. HCl / ethanol / 1 h / Heating View Scheme

1: LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: aq. KOH / ethanol / 3 h / Heating 5: 1.) LDA / 1.) hexane, THF, -70 deg C, 1.5 h, 2.) hexane, THF, from -70 deg C to RT 6: 55 percent / P2O5, MeSO3H / 1 h / Ambient temperature 7: 90 percent / pyridine hydrochloride / 0.5 h / 210 °C 8: 68 percent / K2CO3 / acetone; dimethylformamide / 18 h / Heating 9: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 10: conc. HCl / ethanol / 1 h / Heating View Scheme

1: LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: aq. KOH / ethanol / 3 h / Heating 5: 1.) LDA / 1.) hexane, THF, -70 deg C, 1.5 h, 2.) hexane, THF, from -70 deg C to RT 6: 55 percent / P2O5, MeSO3H / 1 h / Ambient temperature 7: 90 percent / pyridine hydrochloride / 0.5 h / 210 °C 8: 93 percent / K2CO3 / acetone / 3 h / Heating 9: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 10: conc. HCl / ethanol / 1 h / Heating 11: 1.) OsO4, 2.) H2S / 1.) THF, RT, 18 h View Scheme