1.1: sulfuric acid / tetrahydrofuran; water / 10 h / Inert atmosphere; Reflux 2.1: sodium periodate / water; isopropyl alcohol / 20 h / 0 - 20 °C / Inert atmosphere 3.1: iodine; sodium hydrogencarbonate; potassium iodide / dichloromethane; water / 0.5 h / 0 °C / Inert atmosphere 4.1: sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-but-2-ene / tetrahydrofuran; tert-butyl alcohol / 2 h / 0 °C / Inert atmosphere 5.1: diphenylphosphoranyl azide; triethylamine / toluene / 2.5 h / 20 - 110 °C / Inert atmosphere 6.1: toluene / 7 h / 75 °C / Inert atmosphere 7.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 7.2: 1 h / -78 °C / Inert atmosphere 8.1: acetic acid; zinc / ethanol / 3 h / 0 °C / Inert atmosphere 9.1: diethylphosphoryl cyanide; triethylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere 10.1: LiAlH(Ot-Bu)3 / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 11.1: pyridinium p-toluenesulfonate / 15 h / 0 °C / Inert atmosphere 12.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -60 °C / Inert atmosphere 13.1: water; sodium hydroxide / propan-1-ol / Inert atmosphere; Reflux View Scheme

1.1: MsCl; Et3N / CH2Cl2 / 1 h / -40 °C 1.2: 6.81 g / LiBr / CH2Cl2; tetrahydrofuran / 0 - 20 °C 2.1: NaHCO3 / acetonitrile / 0.5 h / 20 °C 2.2: 82 percent / acetonitrile / 3 h / Heating 3.1: (COCl)2; DMSO / CH2Cl2 / 0.33 h / -78 °C 3.2: 75 percent / CH2Cl2 / 3 h / 25 °C 4.1: 81 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C 5.1: MsCl; Et3N / CH2Cl2 / 1 h / -40 °C 5.2: 71 percent / LiCl / tetrahydrofuran; CH2Cl2 / 3 h / 20 °C 6.1: 70 percent / DIBAL-H / CH2Cl2; hexane / 3 h / -78 °C 7.1: NaH / tetrahydrofuran / 1 h / 20 °C 7.2: 53 percent / tetrahydrofuran / 12 h / 70 °C 8.1: (-)-sparteine; nBuLi / toluene; hexane / 1.5 h / -78 °C 9.1: TMEDA; tBuLi / tetrahydrofuran; pentane / 1 h / -78 °C 9.2: tetrahydrofuran; pentane / -78 °C 10.1: 93 mg / 1,2-dichloro-ethane / 3 h / Heating 11.1: 55 percent / MeSO3H; H2O / 16 h / Heating 12.1: Jones reagent / acetone / 0.08 h / 0 °C 13.1: 8.0 mg / aq. NaOH / methanol / 18 h / Heating View Scheme

1.1: NaHCO3 / acetonitrile / 0.5 h / 20 °C 1.2: 82 percent / acetonitrile / 3 h / Heating 2.1: (COCl)2; DMSO / CH2Cl2 / 0.33 h / -78 °C 2.2: 75 percent / CH2Cl2 / 3 h / 25 °C 3.1: 81 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C 4.1: MsCl; Et3N / CH2Cl2 / 1 h / -40 °C 4.2: 71 percent / LiCl / tetrahydrofuran; CH2Cl2 / 3 h / 20 °C 5.1: 70 percent / DIBAL-H / CH2Cl2; hexane / 3 h / -78 °C 6.1: NaH / tetrahydrofuran / 1 h / 20 °C 6.2: 53 percent / tetrahydrofuran / 12 h / 70 °C 7.1: (-)-sparteine; nBuLi / toluene; hexane / 1.5 h / -78 °C 8.1: TMEDA; tBuLi / tetrahydrofuran; pentane / 1 h / -78 °C 8.2: tetrahydrofuran; pentane / -78 °C 9.1: 93 mg / 1,2-dichloro-ethane / 3 h / Heating 10.1: 55 percent / MeSO3H; H2O / 16 h / Heating 11.1: Jones reagent / acetone / 0.08 h / 0 °C 12.1: 8.0 mg / aq. NaOH / methanol / 18 h / Heating View Scheme

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

potassium hydroxide in water 20 h; Ambient temperature; Yield given;

Yield given. Multistep reaction;

1.1: 100 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2 / 12 h 2.1: sodium periodate; ruthenium trichloride hydrate / acetonitrile; H2O; ethyl acetate / 4 h 3.1: 0.56 g / diethyl ether 4.1: 88 percent / m-chloroperbenzoic acid / CH2Cl2 / 48 h 5.1: 99 percent / methanol / 1.5 h / -78 °C 6.1: tri-n-butylphosphine / tetrahydrofuran / 2 h / 20 °C 7.1: 0.31 g / pyridine; hydrogen peroxide / tetrahydrofuran; H2O / -40 - 20 °C 8.1: DIBALH / toluene; tetrahydrofuran / 1 h / -78 °C 8.2: 44 percent / triethylsilane; boron trifluoride etherate / CH2Cl2 / 2.5 h / -78 °C 9.1: lithium hydroxide / tetrahydrofuran; H2O / 12 h / 20 °C 10.1: 15 mg / trifluoroacetic acid / CH2Cl2 / 2 h / Heating View Scheme

1.1: copper(I) bromide / tetrahydrofuran; hexane / 3 h / -78 °C 2.1: 0.42 g / trifluoroacetic acid / 4 h / Heating 3.1: 90 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2 / 12 h 4.1: sodium periodate; ruthenium trichloride hydrate / acetonitrile; H2O; ethyl acetate / 4 h 5.1: 0.56 g / diethyl ether 6.1: 88 percent / m-chloroperbenzoic acid / CH2Cl2 / 48 h 7.1: 99 percent / methanol / 1.5 h / -78 °C 8.1: tri-n-butylphosphine / tetrahydrofuran / 2 h / 20 °C 9.1: 0.31 g / pyridine; hydrogen peroxide / tetrahydrofuran; H2O / -40 - 20 °C 10.1: DIBALH / toluene; tetrahydrofuran / 1 h / -78 °C 10.2: 44 percent / triethylsilane; boron trifluoride etherate / CH2Cl2 / 2.5 h / -78 °C 11.1: lithium hydroxide / tetrahydrofuran; H2O / 12 h / 20 °C 12.1: 15 mg / trifluoroacetic acid / CH2Cl2 / 2 h / Heating View Scheme

1.1: 88 percent / m-chloroperbenzoic acid / CH2Cl2 / 48 h 2.1: 99 percent / methanol / 1.5 h / -78 °C 3.1: tri-n-butylphosphine / tetrahydrofuran / 2 h / 20 °C 4.1: 0.31 g / pyridine; hydrogen peroxide / tetrahydrofuran; H2O / -40 - 20 °C 5.1: DIBALH / toluene; tetrahydrofuran / 1 h / -78 °C 5.2: 44 percent / triethylsilane; boron trifluoride etherate / CH2Cl2 / 2.5 h / -78 °C 6.1: lithium hydroxide / tetrahydrofuran; H2O / 12 h / 20 °C 7.1: 15 mg / trifluoroacetic acid / CH2Cl2 / 2 h / Heating View Scheme

1.1: sodium periodate; ruthenium trichloride hydrate / acetonitrile; H2O; ethyl acetate / 4 h 2.1: 0.56 g / diethyl ether 3.1: 88 percent / m-chloroperbenzoic acid / CH2Cl2 / 48 h 4.1: 99 percent / methanol / 1.5 h / -78 °C 5.1: tri-n-butylphosphine / tetrahydrofuran / 2 h / 20 °C 6.1: 0.31 g / pyridine; hydrogen peroxide / tetrahydrofuran; H2O / -40 - 20 °C 7.1: DIBALH / toluene; tetrahydrofuran / 1 h / -78 °C 7.2: 44 percent / triethylsilane; boron trifluoride etherate / CH2Cl2 / 2.5 h / -78 °C 8.1: lithium hydroxide / tetrahydrofuran; H2O / 12 h / 20 °C 9.1: 15 mg / trifluoroacetic acid / CH2Cl2 / 2 h / Heating View Scheme