1: 1.) triethylamine, ethyl chloroformate, 2.) NH3 gas / 1.) CH2Cl2, -15 - -5 deg C, 1 h, 2.) -15 deg C - room temperature, 0.5 h 2: 62 percent / trifluoroacetic acid / CH2Cl2 / 4 h 3: 90 percent / sodium borohydride, CeCl3 / methanol / 0.02 h 4: 82 percent / acetic acid / 1 h 5: 96 percent / hexamethyldisilazane / pyridine / 0.08 h 6: 54 percent / toluene / 2 h / 370 °C 7: 96 percent / aq. HCl / tetrahydrofuran / 0.08 h 8: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / Ambient temperature 9: 62 percent / trifluoroacetic acid, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C View Scheme

1: 62 percent / trifluoroacetic acid / CH2Cl2 / 4 h 2: 90 percent / sodium borohydride, CeCl3 / methanol / 0.02 h 3: 82 percent / acetic acid / 1 h 4: 96 percent / hexamethyldisilazane / pyridine / 0.08 h 5: 54 percent / toluene / 2 h / 370 °C 6: 96 percent / aq. HCl / tetrahydrofuran / 0.08 h 7: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / Ambient temperature 8: 62 percent / trifluoroacetic acid, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C View Scheme

1: 90 percent / sodium borohydride, CeCl3 / methanol / 0.02 h 2: 82 percent / acetic acid / 1 h 3: 96 percent / hexamethyldisilazane / pyridine / 0.08 h 4: 54 percent / toluene / 2 h / 370 °C 5: 96 percent / aq. HCl / tetrahydrofuran / 0.08 h 6: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / Ambient temperature 7: 62 percent / trifluoroacetic acid, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C View Scheme

1: 82 percent / acetic acid / 1 h 2: 96 percent / hexamethyldisilazane / pyridine / 0.08 h 3: 54 percent / toluene / 2 h / 370 °C 4: 96 percent / aq. HCl / tetrahydrofuran / 0.08 h 5: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / Ambient temperature 6: 62 percent / trifluoroacetic acid, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C View Scheme

1: 96 percent / hexamethyldisilazane / pyridine / 0.08 h 2: 54 percent / toluene / 2 h / 370 °C 3: 96 percent / aq. HCl / tetrahydrofuran / 0.08 h 4: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / Ambient temperature 5: 62 percent / trifluoroacetic acid, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C View Scheme

1: 54 percent / toluene / 2 h / 370 °C 2: 96 percent / aq. HCl / tetrahydrofuran / 0.08 h 3: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / Ambient temperature 4: 62 percent / trifluoroacetic acid, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C View Scheme

1: 76 percent / piperidine / acetic acid; benzene / 6 h / Heating 2: 56 percent / triethylamine / CH2Cl2 / 6 h / Heating 3: 92 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h 4: 84 percent / chromium trioxide, periodic acid / H2O; acetone / 4 h / Ambient temperature 5: 1.) triethylamine, ethyl chloroformate, 2.) NH3 gas / 1.) CH2Cl2, -15 - -5 deg C, 1 h, 2.) -15 deg C - room temperature, 0.5 h 6: 62 percent / trifluoroacetic acid / CH2Cl2 / 4 h 7: 90 percent / sodium borohydride, CeCl3 / methanol / 0.02 h 8: 82 percent / acetic acid / 1 h 9: 96 percent / hexamethyldisilazane / pyridine / 0.08 h 10: 54 percent / toluene / 2 h / 370 °C 11: 96 percent / aq. HCl / tetrahydrofuran / 0.08 h 12: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / Ambient temperature 13: 62 percent / trifluoroacetic acid, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C View Scheme

1: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / Ambient temperature 2: 62 percent / trifluoroacetic acid, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C View Scheme

chloro-trimethyl-silane; sodium iodide in acetonitrile 12 h; Heating;

1: 70 percent / trifluoroacetic acid / 2.5 h / Heating 2: 67 percent / lithium aluminum hydride / diethyl ether / 2.3 h / Heating 3: 1.) sec-butyllithium / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 15 min 4: 56 percent / Swern oxidation View Scheme