hydrogenchloride in methanol; water 1 h; Ambient temperature;

1: 72 percent / benzene / 16 h / Heating 2: 88 percent / H2 / Pd/C / ethyl acetate 4: 97 percent / NaOH / ethanol; H2O / 1.5 h / Ambient temperature 5: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature 6: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C 7: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C 8: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C 9: toluene / 5 h / 90 °C 10: NaOH / methanol / 2 h / Ambient temperature 11: 1.) trimethylsilyl chlorid, lithium isopropylamide / 1.) THF/hexane, -78 degC, 3 h 2.) THF, 0 degC, 3 h 12: 58 percent / H2O2 / pyridine; CH2Cl2; H2O / 18 h / Ambient temperature 13: 90 percent / HCl / methanol; H2O / 1 h / Ambient temperature View Scheme

1: 88 percent / H2 / Pd/C / ethyl acetate 3: 97 percent / NaOH / ethanol; H2O / 1.5 h / Ambient temperature 4: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature 5: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C 6: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C 7: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C 8: toluene / 5 h / 90 °C 9: NaOH / methanol / 2 h / Ambient temperature 10: 1.) trimethylsilyl chlorid, lithium isopropylamide / 1.) THF/hexane, -78 degC, 3 h 2.) THF, 0 degC, 3 h 11: 58 percent / H2O2 / pyridine; CH2Cl2; H2O / 18 h / Ambient temperature 12: 90 percent / HCl / methanol; H2O / 1 h / Ambient temperature View Scheme

1: 91 percent / Na / ethanol / 0.25 h 2: DMSO, oxalyl chloride, Et3N / CH2Cl2 / 0.75 h / -78 °C 3: 72 percent / benzene / 16 h / Heating 4: 88 percent / H2 / Pd/C / ethyl acetate 6: 97 percent / NaOH / ethanol; H2O / 1.5 h / Ambient temperature 7: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature 8: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C 9: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C 10: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C 11: toluene / 5 h / 90 °C 12: NaOH / methanol / 2 h / Ambient temperature 13: 1.) trimethylsilyl chlorid, lithium isopropylamide / 1.) THF/hexane, -78 degC, 3 h 2.) THF, 0 degC, 3 h 14: 58 percent / H2O2 / pyridine; CH2Cl2; H2O / 18 h / Ambient temperature 15: 90 percent / HCl / methanol; H2O / 1 h / Ambient temperature View Scheme

1: 79 percent / H2 / Pd/C / ethanol / 2.5 h / Ambient temperature 2: 91 percent / Na / ethanol / 0.25 h 3: DMSO, oxalyl chloride, Et3N / CH2Cl2 / 0.75 h / -78 °C 4: 72 percent / benzene / 16 h / Heating 5: 88 percent / H2 / Pd/C / ethyl acetate 7: 97 percent / NaOH / ethanol; H2O / 1.5 h / Ambient temperature 8: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature 9: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C 10: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C 11: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C 12: toluene / 5 h / 90 °C 13: NaOH / methanol / 2 h / Ambient temperature 14: 1.) trimethylsilyl chlorid, lithium isopropylamide / 1.) THF/hexane, -78 degC, 3 h 2.) THF, 0 degC, 3 h 15: 58 percent / H2O2 / pyridine; CH2Cl2; H2O / 18 h / Ambient temperature 16: 90 percent / HCl / methanol; H2O / 1 h / Ambient temperature View Scheme

1: 71 percent / 4-dimethylaminopyridine, Et3N / CH2Cl2 / 15 h / 0 °C 2: 75 percent / potassium t-butoxide 3: 90 percent / HBr / H2O / 16 h / Heating 4: 67 percent / dioxane / 16 h / Heating 5: 57 percent / NaH / tetrahydrofuran / 1.08 h 6: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C 7: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C 8: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C 9: toluene / 5 h / 90 °C 10: NaOH / methanol / 2 h / Ambient temperature 11: 1.) trimethylsilyl chlorid, lithium isopropylamide / 1.) THF/hexane, -78 degC, 3 h 2.) THF, 0 degC, 3 h 12: 58 percent / H2O2 / pyridine; CH2Cl2; H2O / 18 h / Ambient temperature 13: 90 percent / HCl / methanol; H2O / 1 h / Ambient temperature View Scheme

1: 67 percent / dioxane / 16 h / Heating 2: 57 percent / NaH / tetrahydrofuran / 1.08 h 3: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C 4: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C 5: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C 6: toluene / 5 h / 90 °C 7: NaOH / methanol / 2 h / Ambient temperature 8: 1.) trimethylsilyl chlorid, lithium isopropylamide / 1.) THF/hexane, -78 degC, 3 h 2.) THF, 0 degC, 3 h 9: 58 percent / H2O2 / pyridine; CH2Cl2; H2O / 18 h / Ambient temperature 10: 90 percent / HCl / methanol; H2O / 1 h / Ambient temperature View Scheme

2: 97 percent / NaOH / ethanol; H2O / 1.5 h / Ambient temperature 3: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature 4: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C 5: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C 6: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C 7: toluene / 5 h / 90 °C 8: NaOH / methanol / 2 h / Ambient temperature 9: 1.) trimethylsilyl chlorid, lithium isopropylamide / 1.) THF/hexane, -78 degC, 3 h 2.) THF, 0 degC, 3 h 10: 58 percent / H2O2 / pyridine; CH2Cl2; H2O / 18 h / Ambient temperature 11: 90 percent / HCl / methanol; H2O / 1 h / Ambient temperature View Scheme

1: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C 2: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C 3: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C 4: toluene / 5 h / 90 °C 5: NaOH / methanol / 2 h / Ambient temperature 6: 1.) trimethylsilyl chlorid, lithium isopropylamide / 1.) THF/hexane, -78 degC, 3 h 2.) THF, 0 degC, 3 h 7: 58 percent / H2O2 / pyridine; CH2Cl2; H2O / 18 h / Ambient temperature 8: 90 percent / HCl / methanol; H2O / 1 h / Ambient temperature View Scheme

1: 75 percent / potassium t-butoxide 2: 90 percent / HBr / H2O / 16 h / Heating 3: 67 percent / dioxane / 16 h / Heating 4: 57 percent / NaH / tetrahydrofuran / 1.08 h 5: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C 6: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C 7: H2O2, m-chloroperoxybenzoic acid / CHCl3; H2O / 0.75 h / -50 - 0 °C 8: toluene / 5 h / 90 °C 9: NaOH / methanol / 2 h / Ambient temperature 10: 1.) trimethylsilyl chlorid, lithium isopropylamide / 1.) THF/hexane, -78 degC, 3 h 2.) THF, 0 degC, 3 h 11: 58 percent / H2O2 / pyridine; CH2Cl2; H2O / 18 h / Ambient temperature 12: 90 percent / HCl / methanol; H2O / 1 h / Ambient temperature View Scheme