1: 1.) NaOH / 1.) dioxane, water, 70 deg C, 16 h, 2.) dioxane, water, room temperature, 2 h 2: 16 mg / diethyl ether 3: CrO3, H2SO4 / acetone / 1 h / 0 °C 4: 9 mg / diethyl ether 5: KOH / tetrahydrofuran / 12 h / Ambient temperature 6: 4.5 mg / trifluoroacetic acid / CH2Cl2 / 12 h View Scheme

1: 63 percent / zinc, TiCl4 / tetrahydrofuran; CH2Cl2 / 0 °C 2: 1.) NaOH / 1.) dioxane, water, 70 deg C, 16 h, 2.) dioxane, water, room temperature, 2 h 3: 16 mg / diethyl ether 4: CrO3, H2SO4 / acetone / 1 h / 0 °C 5: 9 mg / diethyl ether 6: KOH / tetrahydrofuran / 12 h / Ambient temperature 7: 4.5 mg / trifluoroacetic acid / CH2Cl2 / 12 h View Scheme

1: bromodimethylborane / CH2Cl2 / 0.75 h / -78 °C / other reagents: TsOH, SnCl2*H2O 2: 1.) cerium trichloride / 1.) THF, ether, 45 min, 2.) THF, ether, -78 deg C, 25 min 3: 80 percent / tetra-n-propylammonium perruthenate, molecular sieves 3A, N-methylmorpholine N-oxide / CH2Cl2 / 0.5 h 4: 63 percent / zinc, TiCl4 / tetrahydrofuran; CH2Cl2 / 0 °C 5: 1.) NaOH / 1.) dioxane, water, 70 deg C, 16 h, 2.) dioxane, water, room temperature, 2 h 6: 16 mg / diethyl ether 7: CrO3, H2SO4 / acetone / 1 h / 0 °C 8: 9 mg / diethyl ether 9: KOH / tetrahydrofuran / 12 h / Ambient temperature 10: 4.5 mg / trifluoroacetic acid / CH2Cl2 / 12 h View Scheme

1: diisopropylethylamine / CH2Cl2 / 3 h / Ambient temperature 2: 95 percent / Fe(O), Et3N, HMPA / diethyl ether; tetrahydrofuran / 1.) r.t., 10 min, 2.) r.t., 2 h 3: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C 5: tetrahydrofuran; hexane 6: 97 percent / CF3COOH / CH2Cl2 / 1 h / Ambient temperature 7: PDC, 4 Angstroem molecular sieves / dimethylformamide / 20 h / Ambient temperature 9: 3 N LiOH / methanol / 1 h / Heating 10: Li, liq. NH3 / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1.1: diphenylphosphoranyl azide; triethylamine / toluene / 2.5 h / 20 - 110 °C / Inert atmosphere 2.1: toluene / 7 h / 75 °C / Inert atmosphere 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: acetic acid; zinc / ethanol / 3 h / 0 °C / Inert atmosphere 5.1: diethylphosphoryl cyanide; triethylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere 6.1: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 7.1: pyridinium p-toluenesulfonate / 15 h / 0 °C / Inert atmosphere 8.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -60 °C / Inert atmosphere 9.1: water; sodium hydroxide / propan-1-ol / Inert atmosphere; Reflux View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: acetic acid; zinc / ethanol / 3 h / 0 °C / Inert atmosphere 3.1: diethylphosphoryl cyanide; triethylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere 4.1: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 5.1: pyridinium p-toluenesulfonate / 15 h / 0 °C / Inert atmosphere 6.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -60 °C / Inert atmosphere 7.1: water; sodium hydroxide / propan-1-ol / Inert atmosphere; Reflux View Scheme

1: diethylphosphoryl cyanide; triethylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere 2: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 3: pyridinium p-toluenesulfonate / 15 h / 0 °C / Inert atmosphere 4: boron trifluoride diethyl etherate / dichloromethane / 1 h / -60 °C / Inert atmosphere 5: water; sodium hydroxide / propan-1-ol / Inert atmosphere; Reflux View Scheme

1.1: sodium periodate / water; isopropyl alcohol / 20 h / 0 - 20 °C / Inert atmosphere 2.1: iodine; sodium hydrogencarbonate; potassium iodide / dichloromethane; water / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-but-2-ene / tetrahydrofuran; tert-butyl alcohol / 2 h / 0 °C / Inert atmosphere 4.1: diphenylphosphoranyl azide; triethylamine / toluene / 2.5 h / 20 - 110 °C / Inert atmosphere 5.1: toluene / 7 h / 75 °C / Inert atmosphere 6.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 6.2: 1 h / -78 °C / Inert atmosphere 7.1: acetic acid; zinc / ethanol / 3 h / 0 °C / Inert atmosphere 8.1: diethylphosphoryl cyanide; triethylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere 9.1: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 10.1: pyridinium p-toluenesulfonate / 15 h / 0 °C / Inert atmosphere 11.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -60 °C / Inert atmosphere 12.1: water; sodium hydroxide / propan-1-ol / Inert atmosphere; Reflux View Scheme

1.1: iodine; sodium hydrogencarbonate; potassium iodide / dichloromethane; water / 0.5 h / 0 °C / Inert atmosphere 2.1: sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-but-2-ene / tetrahydrofuran; tert-butyl alcohol / 2 h / 0 °C / Inert atmosphere 3.1: diphenylphosphoranyl azide; triethylamine / toluene / 2.5 h / 20 - 110 °C / Inert atmosphere 4.1: toluene / 7 h / 75 °C / Inert atmosphere 5.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 5.2: 1 h / -78 °C / Inert atmosphere 6.1: acetic acid; zinc / ethanol / 3 h / 0 °C / Inert atmosphere 7.1: diethylphosphoryl cyanide; triethylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere 8.1: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 9.1: pyridinium p-toluenesulfonate / 15 h / 0 °C / Inert atmosphere 10.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -60 °C / Inert atmosphere 11.1: water; sodium hydroxide / propan-1-ol / Inert atmosphere; Reflux View Scheme

1.1: dihydrogen peroxide; sodium hydroxide / methanol; water / 0 °C / Inert atmosphere 2.1: sulfuric acid / tetrahydrofuran; water / 10 h / Inert atmosphere; Reflux 3.1: sodium periodate / water; isopropyl alcohol / 20 h / 0 - 20 °C / Inert atmosphere 4.1: iodine; sodium hydrogencarbonate; potassium iodide / dichloromethane; water / 0.5 h / 0 °C / Inert atmosphere 5.1: sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-but-2-ene / tetrahydrofuran; tert-butyl alcohol / 2 h / 0 °C / Inert atmosphere 6.1: diphenylphosphoranyl azide; triethylamine / toluene / 2.5 h / 20 - 110 °C / Inert atmosphere 7.1: toluene / 7 h / 75 °C / Inert atmosphere 8.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 8.2: 1 h / -78 °C / Inert atmosphere 9.1: acetic acid; zinc / ethanol / 3 h / 0 °C / Inert atmosphere 10.1: diethylphosphoryl cyanide; triethylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere 11.1: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 12.1: pyridinium p-toluenesulfonate / 15 h / 0 °C / Inert atmosphere 13.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -60 °C / Inert atmosphere 14.1: water; sodium hydroxide / propan-1-ol / Inert atmosphere; Reflux View Scheme