1: thionyl chloride / toluene / 1 h / 80 °C 2: ethanol; H2O / 12 h / Heating 3: 76 percent / aq. KOH / ethanol / 3 h / Heating 4: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 5: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 6: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 7: 90 percent / K2CO3 / acetone / 3 h / Heating 8: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 9: conc. HCl / ethanol / 1 h / Heating View Scheme

1: thionyl chloride / toluene / 1 h / 80 °C 2: ethanol; H2O / 12 h / Heating 3: 76 percent / aq. KOH / ethanol / 3 h / Heating 4: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 5: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 6: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 7: 60 percent / K2CO3 / acetone; dimethylformamide / 18 h / Heating 8: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 9: 68 percent / conc. HCl / ethanol / 1 h / Heating View Scheme

1: thionyl chloride / toluene / 1 h / 80 °C 2: ethanol; H2O / 12 h / Heating 3: 76 percent / aq. KOH / ethanol / 3 h / Heating 4: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 5: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 6: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 7: 60 percent / K2CO3 / acetone; dimethylformamide / 18 h / Heating 8: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 9: conc. HCl / ethanol / 1 h / Heating View Scheme

1: thionyl chloride / toluene / 1 h / 80 °C 2: ethanol; H2O / 12 h / Heating 3: 76 percent / aq. KOH / ethanol / 3 h / Heating 4: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 5: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 6: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 7: 90 percent / K2CO3 / acetone / 3 h / Heating 8: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 9: conc. HCl / ethanol / 1 h / Heating View Scheme

1: thionyl chloride / toluene / 1 h / 80 °C 2: ethanol; H2O / 12 h / Heating 3: 76 percent / aq. KOH / ethanol / 3 h / Heating 4: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 5: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 6: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 7: 90 percent / K2CO3 / acetone / 3 h / Heating 8: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 9: conc. HCl / ethanol / 1 h / Heating 10: 1.) OsO4, 2.) H2S / 1.) THF, RT, 18 h View Scheme