1: 96 percent / Et3N / CH2Cl2 / 2 h / 0 °C 2: 93 percent / NaBH4, tert-butyl alcohol / CH2Cl2 / 70 h / Heating 3: 1.) borane, 2-methyl-2-butene, 2.) 30percent aq. H2O2 / 1.) THF, 0 deg C, 1 h, 2.) THF, H2O, 0 deg C, 30 min 4: Et3N / CH2Cl2 / 24 h / 0 °C 5: Et3N / tetrahydrofuran / 48 h / 80 °C View Scheme

1: 93 percent / NaBH4, tert-butyl alcohol / CH2Cl2 / 70 h / Heating 2: 1.) borane, 2-methyl-2-butene, 2.) 30percent aq. H2O2 / 1.) THF, 0 deg C, 1 h, 2.) THF, H2O, 0 deg C, 30 min 3: Et3N / CH2Cl2 / 24 h / 0 °C 4: Et3N / tetrahydrofuran / 48 h / 80 °C View Scheme

1: 93 percent / NaBH4, tert-butyl alcohol / CH2Cl2 / 70 h / Heating 2: 1.) borane, 2-methyl-2-butene, 2.) 30percent aq. H2O2 / 1.) THF, 0 deg C, 1 h, 2.) THF, H2O, 0 deg C, 30 min 3: Et3N / CH2Cl2 / 24 h / 0 °C 4: Et3N / tetrahydrofuran / 48 h / 80 °C View Scheme

1: potassium hydroxide / methanol / 2 h / Heating 2: 95 percent / triphenylphosphane / CCl4 / 2 h / Heating 3: 91 percent / 1 h / 130 °C View Scheme

1: 92 percent / pyridine 2: 85 percent / dimethylsulfoxide / 2 h / 80 °C 3: 81 percent / 20percent KOH / bis-(2-hydroxy-ethyl) ether / 1 h / Heating 4: 98 percent / diethyl ether 5: 84 percent / DIBAL-H / toluene / 1 h / 20 °C 6: 98 percent / pyridine 7: 68 percent / ozone; triphenylphosphane / CH2Cl2; methanol 8: hydroxylamine hydrochloride; sodium acetate / ethanol 9: 1.52 g / sodium acetate / acetic anhydride / Heating 10: potassium hydroxide / methanol / 2 h / Heating 11: 95 percent / triphenylphosphane / CCl4 / 2 h / Heating 12: 91 percent / 1 h / 130 °C View Scheme

1: 90 percent / pyridine 2: 84 percent / dimethylsulfoxide / 2 h / 80 °C 3: 79 percent / 20percent KOH / bis-(2-hydroxy-ethyl) ether / 1 h / Heating 4: 97 percent / diethyl ether 5: 80 percent / DIBAL-H / toluene / 1 h / 20 °C 6: 98 percent / pyridine 7: 69 percent / ozone; triphenylphosphane / CH2Cl2; methanol 8: hydroxylamine hydrochloride; sodium acetate / ethanol 9: 1.19 g / sodium acetate / acetic anhydride / Heating 10: potassium hydroxide / methanol / 2 h / Heating 11: 95 percent / triphenylphosphane / CCl4 / 2 h / Heating 12: 91 percent / 1 h / 130 °C View Scheme

1.1: lithium diisopropylamide / tetrahydrofuran / 0.08 h / -78 °C 1.2: trimethylchlorosilane / tetrahydrofuran / 3 h / Heating 1.3: methanol / 0.17 h / 20 °C 2.1: 97 percent / diethyl ether 3.1: 91 percent / DIBAL-H / toluene / 1 h / 20 °C 4.1: 90 percent / pyridine 5.1: 84 percent / dimethylsulfoxide / 2 h / 80 °C 6.1: 79 percent / 20percent KOH / bis-(2-hydroxy-ethyl) ether / 1 h / Heating 7.1: 97 percent / diethyl ether 8.1: 80 percent / DIBAL-H / toluene / 1 h / 20 °C 9.1: 98 percent / pyridine 10.1: 69 percent / ozone; triphenylphosphane / CH2Cl2; methanol 11.1: hydroxylamine hydrochloride; sodium acetate / ethanol 12.1: 1.19 g / sodium acetate / acetic anhydride / Heating 13.1: potassium hydroxide / methanol / 2 h / Heating 14.1: 95 percent / triphenylphosphane / CCl4 / 2 h / Heating 15.1: 91 percent / 1 h / 130 °C View Scheme

1.1: lithium diisopropylamide / tetrahydrofuran / 0.08 h / -78 °C 1.2: trimethylchlorosilane / tetrahydrofuran / 3 h / Heating 1.3: 63 percent / methanol / 0.17 h / 20 °C 2.1: 97 percent / diethyl ether 3.1: 89 percent / DIBAL-H / toluene / 1 h / 20 °C 4.1: 92 percent / pyridine 5.1: 85 percent / dimethylsulfoxide / 2 h / 80 °C 6.1: 81 percent / 20percent KOH / bis-(2-hydroxy-ethyl) ether / 1 h / Heating 7.1: 98 percent / diethyl ether 8.1: 84 percent / DIBAL-H / toluene / 1 h / 20 °C 9.1: 98 percent / pyridine 10.1: 68 percent / ozone; triphenylphosphane / CH2Cl2; methanol 11.1: hydroxylamine hydrochloride; sodium acetate / ethanol 12.1: 1.52 g / sodium acetate / acetic anhydride / Heating 13.1: potassium hydroxide / methanol / 2 h / Heating 14.1: 95 percent / triphenylphosphane / CCl4 / 2 h / Heating 15.1: 91 percent / 1 h / 130 °C View Scheme

1: 97 percent / diethyl ether 2: 89 percent / DIBAL-H / toluene / 1 h / 20 °C 3: 92 percent / pyridine 4: 85 percent / dimethylsulfoxide / 2 h / 80 °C 5: 81 percent / 20percent KOH / bis-(2-hydroxy-ethyl) ether / 1 h / Heating 6: 98 percent / diethyl ether 7: 84 percent / DIBAL-H / toluene / 1 h / 20 °C 8: 98 percent / pyridine 9: 68 percent / ozone; triphenylphosphane / CH2Cl2; methanol 10: hydroxylamine hydrochloride; sodium acetate / ethanol 11: 1.52 g / sodium acetate / acetic anhydride / Heating 12: potassium hydroxide / methanol / 2 h / Heating 13: 95 percent / triphenylphosphane / CCl4 / 2 h / Heating 14: 91 percent / 1 h / 130 °C View Scheme

1: 97 percent / diethyl ether 2: 91 percent / DIBAL-H / toluene / 1 h / 20 °C 3: 90 percent / pyridine 4: 84 percent / dimethylsulfoxide / 2 h / 80 °C 5: 79 percent / 20percent KOH / bis-(2-hydroxy-ethyl) ether / 1 h / Heating 6: 97 percent / diethyl ether 7: 80 percent / DIBAL-H / toluene / 1 h / 20 °C 8: 98 percent / pyridine 9: 69 percent / ozone; triphenylphosphane / CH2Cl2; methanol 10: hydroxylamine hydrochloride; sodium acetate / ethanol 11: 1.19 g / sodium acetate / acetic anhydride / Heating 12: potassium hydroxide / methanol / 2 h / Heating 13: 95 percent / triphenylphosphane / CCl4 / 2 h / Heating 14: 91 percent / 1 h / 130 °C View Scheme