1: 68 percent / lead tetra-acetate / H2O; acetic acid / 1 h / Heating 2: 66 percent / toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 3: 69 percent / H2 / 10percent palladized charcoal / tetrahydrofuran 4: 41 percent / 1.) trifluoroacetic acid / methanol; CH2Cl2 / 1.) 2-3 deg C 70 min, 2.) 18 deg C 2 min, 20 min 5: 100 percent / H2 / 10percent palladized charcoal / acetic acid / 4 h / Ambient temperature 6: sodium amalgam, aq. acetic acid / 18 h / 37 °C / enzymes from Euglena gracilis 7: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min 8: 0.5 h / coproporphyrinogen-III oxidase (from Euglena gracilis) View Scheme

sodium in tetrahydrofuran T=20°C; 1.16667 h;

methanol; sodium

1: 68 percent / lead tetra-acetate / H2O; acetic acid / 1 h / Heating 2: 66 percent / toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 3: 69 percent / H2 / 10percent palladized charcoal / tetrahydrofuran 4: 41 percent / 1.) trifluoroacetic acid / methanol; CH2Cl2 / 1.) 2-3 deg C 70 min, 2.) 18 deg C 2 min, 20 min 5: 100 percent / H2 / 10percent palladized charcoal / acetic acid / 4 h / Ambient temperature 6: sodium amalgam, aq. acetic acid / 18 h / 37 °C / enzymes from Euglena gracilis 7: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min View Scheme