1: 1.) NaH / 1.) dioxane, MeOH, reflux; 2.) reflux, 90 min 2: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating 3: OsO4, NaIO4 / diethyl ether; H2O 4: LAH / diethyl ether 5: 1.) pyridine; 2.) 6N HCl aq. View Scheme

1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 1.2: tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: TiCl4 / CH2Cl2 / 0.17 h / -78 °C 3.1: 63 percent / p-TsOH; 4 Angstroem molecular sieves / benzene / 1 h / Heating 4.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 4.2: tetrahydrofuran; hexane / 0.5 h / -15 - 20 °C 5.1: MCPBA / hexane / 4 h / 20 °C 5.2: 0.8 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 6.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 7.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C 7.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating View Scheme

1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 1.2: tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: TiCl4 / CH2Cl2 / 0.17 h / -78 °C 3.1: HMDS / CH2Cl2 / 4 h / -78 - 20 °C 4.1: MCPBA / hexane / 4 h / 20 °C 4.2: 0.4 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 5.1: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C View Scheme

1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 1.2: tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: TiCl4 / CH2Cl2 / 0.17 h / -78 °C 3.1: HMDS / CH2Cl2 / 4 h / -78 - 20 °C 4.1: MCPBA / hexane / 4 h / 20 °C 4.2: 0.4 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 5.1: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 6.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C 6.2: 75 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating View Scheme

1: 1.) NaH / 1.) dioxane, MeOH, reflux; 2.) reflux, 90 min 2: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating 3: LiAlH4 / diethyl ether / 1 h / below 10 deg C 4: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating 5: OsO4, NaIO4 / diethyl ether; H2O / 7 h 6: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C 7: pyridine / Ambient temperature 8: 75 percent AcOH / 1 h / 30 °C 9: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min 10: NaOAc / 0.67 h / 130 °C 11: 1 percent NaOMe / methanol / 1 h / Ambient temperature 12: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C 13: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h 14: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature 15: 84 percent / TMSCl, NaI / acetonitrile / -10 °C 16: 86 percent / sodium naphtalenide / 0.08 h / -70 °C 17: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature 18: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min View Scheme