1: 94.6 percent / Et3N / diethyl ether / 0.5 h / Ambient temperature 2: 78 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h 3: 98.4 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 4: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 5: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating 6: conc. H2SO4 / ethanol / 0.33 h / Heating View Scheme

1: 94.6 percent / Et3N / diethyl ether / 0.5 h / Ambient temperature 2: 78 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h 3: 98.4 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 4: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 5: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

thionyl chloride; N,N-dimethyl-formamide in tetrachloromethane T=100°C;

thionyl chloride in N,N-dimethyl-formamide 2 h; Heating;

1.1: toluene-4-sulfonic acid / toluene / 8 h / |Reflux 2.1: sodium hydroxide / ethanol / 1 h / 20 °C 3.1: potassium hydroxide; silver nitrate / water / 0.33 h / 20 °C 3.2: 1.5 h / |Cooling with ice 4.1: water; sodium hydroxide / 2 h / 45 °C 5.1: thionyl chloride / 1 h / |Reflux View Scheme

1.1: sodium hydroxide / ethanol / 1 h / 20 °C 2.1: potassium hydroxide; silver nitrate / water / 0.33 h / 20 °C 2.2: 1.5 h / |Cooling with ice 3.1: water; sodium hydroxide / 2 h / 45 °C 4.1: thionyl chloride / 1 h / |Reflux View Scheme

1.1: potassium hydroxide; silver nitrate / water / 0.33 h / 20 °C 1.2: 1.5 h / |Cooling with ice 2.1: water; sodium hydroxide / 2 h / 45 °C 3.1: thionyl chloride / 1 h / |Reflux View Scheme

1: 94.6 percent / Et3N / diethyl ether / 0.5 h / Ambient temperature 2: 78 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h 3: 97.8 percent / LDA / tetrahydrofuran / 1.) 1 h, -78 deg C, 2.) 2 h, ice bath, 3.) 0.5 h, r.t. 4: 100 percent / NaIO4 / H2O; methanol / 20 h / Ambient temperature 5: LDA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 30 min, ice bath 6: Al-Hg / tetrahydrofuran; H2O / 6 h / Heating View Scheme

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