1: 1.) ozone, 2.) NaBH4 / 1.) EtOH, -78 deg C, 3 min, 2.) EtOH, H2O, -78 to 24 deg C, 4 h 2: 89 percent / Et3N / CH2Cl2 / 0.42 h / 0 °C 3: 75 percent / H2 / 10percent Pd/C / tetrahydrofuran / 7 h / 24 °C / 760 Torr 4: 100 percent / HCl / ethyl acetate / 0.17 h / 24 °C 5: 71 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide, K2CO3 / dimethylformamide / 20 h / 24 °C 6: 91 percent / NaH / tetrahydrofuran; dimethylformamide / 0.42 h / 24 °C View Scheme

1: 1.) ozone, 2.) NaBH4 / 1.) EtOH, -78 deg C, 3 min, 2.) EtOH, H2O, -78 to 24 deg C, 4 h 2: 89 percent / Et3N / CH2Cl2 / 0.42 h / 0 °C 3: 75 percent / H2 / 10percent Pd/C / tetrahydrofuran / 7 h / 24 °C / 760 Torr 4: 100 percent / HCl / ethyl acetate / 0.17 h / 24 °C 5: 84 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide, Et3N / dimethylformamide / 45 h / 24 °C 6: 90 percent / NaH / tetrahydrofuran / 0.42 h / 24 °C View Scheme

1: 1.) ozone, 2.) NaBH4 / 1.) EtOH, -78 deg C, 3 min, 2.) EtOH, H2O, -78 to 24 deg C, 4 h 2: 89 percent / Et3N / CH2Cl2 / 0.42 h / 0 °C 3: 75 percent / H2 / 10percent Pd/C / tetrahydrofuran / 7 h / 24 °C / 760 Torr 4: 100 percent / HCl / ethyl acetate / 0.17 h / 24 °C 5: 71 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide, K2CO3 / dimethylformamide / 20 h / 24 °C View Scheme

Multi-step reaction with 5 steps 1: 1.) ozone, 2.) NaBH4 / 1.) EtOH, -78 deg C, 3 min, 2.) EtOH, H2O, -78 to 24 deg C, 4 h2: 89 percent / Et3N / CH2Cl2 / 0.42 h / 0 °C3: 75 percent / H2 / 10percent Pd/C / tetrahydrofuran / 7 h / 24 °C / 760 Torr4: 100 percent / HCl / ethyl acetate / 0.17 h / 24 °C5: 84 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide, Et3N / dimethylformamide / 45 h / 24 °C