ammonium acetate in water T=37°C; 24 h; bacterial cells Erwinia herbicola, pH 8.5;

ammonium hydroxide; tyrosine phenollylase; pyridoxal 5'-phosphate; ammonium acetate; 2-hydroxyethanethiol in water Ambient temperature;

fluorine in trifluoroacetic acid T=0 - 4°C; 0.5 h;

1: 95 percent / imidazole / dimethylformamide / Ambient temperature 2: 1.) 1.4M sec-butyllithium / 1.) THF, cyclohexane, 30 min at -78 deg C; 2.) THF, cyclohexane, 30 min at room temp. 3: 85 percent / KF / dimethylformamide / 18 h / Ambient temperature 4: 83 percent / NaBH4 / methanol / 0.5 h / Ambient temperature 5: 95 percent / pyridine, SOBr2 / CH2Cl2 / 3 h / Heating 6: 1.) lithium diisopropylamide / 1.) THF, hexane, 40 min, -78 deg C; 2.) THF, hexane, 18 h at room temp. 7: 55percent HI / 1.5 h / Heating View Scheme

1: 85 percent / KF / dimethylformamide / 18 h / Ambient temperature 2: 83 percent / NaBH4 / methanol / 0.5 h / Ambient temperature 3: 95 percent / pyridine, SOBr2 / CH2Cl2 / 3 h / Heating 4: 1.) lithium diisopropylamide / 1.) THF, hexane, 40 min, -78 deg C; 2.) THF, hexane, 18 h at room temp. 5: 55percent HI / 1.5 h / Heating View Scheme

1: 83 percent / NaBH4 / methanol / 0.5 h / Ambient temperature 2: 95 percent / pyridine, SOBr2 / CH2Cl2 / 3 h / Heating 3: 1.) lithium diisopropylamide / 1.) THF, hexane, 40 min, -78 deg C; 2.) THF, hexane, 18 h at room temp. 4: 55percent HI / 1.5 h / Heating View Scheme

1: 95 percent / pyridine, SOBr2 / CH2Cl2 / 3 h / Heating 2: 1.) lithium diisopropylamide / 1.) THF, hexane, 40 min, -78 deg C; 2.) THF, hexane, 18 h at room temp. 3: 55percent HI / 1.5 h / Heating View Scheme

1: 1.) 1.4M sec-butyllithium / 1.) THF, cyclohexane, 30 min at -78 deg C; 2.) THF, cyclohexane, 30 min at room temp. 2: 85 percent / KF / dimethylformamide / 18 h / Ambient temperature 3: 83 percent / NaBH4 / methanol / 0.5 h / Ambient temperature 4: 95 percent / pyridine, SOBr2 / CH2Cl2 / 3 h / Heating 5: 1.) lithium diisopropylamide / 1.) THF, hexane, 40 min, -78 deg C; 2.) THF, hexane, 18 h at room temp. 6: 55percent HI / 1.5 h / Heating View Scheme

1: 5.2 g / pyridine / 0.17 h 2: fluorine / trifluoroacetic acid / 0.5 h / 0 - 4 °C View Scheme

1: 88 percent / HCl gas 2: 5.2 g / pyridine / 0.17 h 3: fluorine / trifluoroacetic acid / 0.5 h / 0 - 4 °C View Scheme