1: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 2: conc. HCl / ethanol / 1 h / Heating 3: 1.) OsO4, 2.) H2S / 1.) THF, RT, 18 h 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

1: 93 percent / K2CO3 / acetone / 3 h / Heating 2: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 3: conc. HCl / ethanol / 1 h / Heating 4: 1.) OsO4, 2.) H2S / 1.) THF, RT, 18 h View Scheme

1: 90 percent / pyridine hydrochloride / 0.5 h / 210 °C 2: 93 percent / K2CO3 / acetone / 3 h / Heating 3: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 4: conc. HCl / ethanol / 1 h / Heating 5: 1.) OsO4, 2.) H2S / 1.) THF, RT, 18 h View Scheme

1: 1.) LDA / 1.) hexane, THF, -70 deg C, 1.5 h, 2.) hexane, THF, from -70 deg C to RT 2: 55 percent / P2O5, MeSO3H / 1 h / Ambient temperature 3: 90 percent / pyridine hydrochloride / 0.5 h / 210 °C 4: 93 percent / K2CO3 / acetone / 3 h / Heating 5: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 6: conc. HCl / ethanol / 1 h / Heating 7: 1.) OsO4, 2.) H2S / 1.) THF, RT, 18 h View Scheme

1: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 2: conc. HCl / ethanol / 1 h / Heating 3: 1.) OsO4, 2.) H2S / 1.) THF, RT, 18 h View Scheme

1: 55 percent / P2O5, MeSO3H / 1 h / Ambient temperature 2: 90 percent / pyridine hydrochloride / 0.5 h / 210 °C 3: 93 percent / K2CO3 / acetone / 3 h / Heating 4: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 5: conc. HCl / ethanol / 1 h / Heating 6: 1.) OsO4, 2.) H2S / 1.) THF, RT, 18 h View Scheme

osmium(VIII) oxide; hydrogen sulfide 1.) THF, RT, 18 h; Yield given. Multistep reaction;