ammonia; pen V amidase in water pH=8.2; Enzymatic reaction;

hydrogen; palladium on activated charcoal in ethyl acetate 3 h; Ambient temperature;

hydrazine in tetrahydrofuran

1: Na2S*9H2O / acetone; H2O 2: DCC 3: N2H4 / tetrahydrofuran View Scheme

1: DCC 2: N2H4 / tetrahydrofuran View Scheme

1: 90 percent / 2,6-lutidine / tetrahydrofuran / 2 h / -78 °C 2: 1) ozone, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min 3: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h 4: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C 5: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C 6: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature 7: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C 8: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 9: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme

1: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 2: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme

1: 1) ozone, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min 2: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h 3: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C 4: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C 5: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature 6: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C 7: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 8: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme

1: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h 2: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C 3: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C 4: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature 5: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C 6: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 7: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme

1: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C 2: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C 3: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature 4: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C 5: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 6: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme