1: 99 percent / H2 / 10percent Pd/C / tetrahydrofuran 2: 60 percent / trimethyl orthoformate / trifluoroacetic acid / 0.37 h / 0 °C 3: 58 percent / 1.) trifluoroacetic acid, 2.) sodium acetate / methanol; CH2Cl2 / 1.) 2-3 deg C 90 min, 2.) 18 deg C 5 min, 3.) 50 min 4: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min 5: 0.5 h / coproporphyrinogen-III oxidase (from Euglena gracilis) View Scheme

1: 60 percent / trimethyl orthoformate / trifluoroacetic acid / 0.37 h / 0 °C 2: 58 percent / 1.) trifluoroacetic acid, 2.) sodium acetate / methanol; CH2Cl2 / 1.) 2-3 deg C 90 min, 2.) 18 deg C 5 min, 3.) 50 min 3: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min 4: 0.5 h / coproporphyrinogen-III oxidase (from Euglena gracilis) View Scheme

1: 58 percent / 1.) trifluoroacetic acid, 2.) sodium acetate / methanol; CH2Cl2 / 1.) 2-3 deg C 90 min, 2.) 18 deg C 5 min, 3.) 50 min 2: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min 3: 0.5 h / coproporphyrinogen-III oxidase (from Euglena gracilis) View Scheme

1: 90 percent / POCl3 / dimethylformamide / 0.75 h / 40 °C 2: 96 percent / KOH / H2O; dimethylformamide / 0.25 h / 20 °C 3: 99 percent / bromine / CCl4 / 1 h / 20 °C 4: 70 percent / aq. ethanol / 1 h / Heating 5: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere 6: 1.) 40percent HBr 2.) benzoyl chloride / 1.) glac.AcOH, 8 h, 20 degC 2.) DMF, 24 h, 20 degC 7: 90 percent / HBr / diethyl ether / 0.17 h 8: 88 percent / HBr / methanol / 0.17 h 9: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 10: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

1: 1.) 40percent HBr 2.) benzoyl chloride / 1.) glac.AcOH, 8 h, 20 degC 2.) DMF, 24 h, 20 degC 2: 90 percent / HBr / diethyl ether / 0.17 h 3: 88 percent / HBr / methanol / 0.17 h 4: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 5: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

1: 99 percent / bromine / CCl4 / 1 h / 20 °C 2: 70 percent / aq. ethanol / 1 h / Heating 3: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere 4: 1.) 40percent HBr 2.) benzoyl chloride / 1.) glac.AcOH, 8 h, 20 degC 2.) DMF, 24 h, 20 degC 5: 90 percent / HBr / diethyl ether / 0.17 h 6: 88 percent / HBr / methanol / 0.17 h 7: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 8: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

1: 96 percent / KOH / H2O; dimethylformamide / 0.25 h / 20 °C 2: 99 percent / bromine / CCl4 / 1 h / 20 °C 3: 70 percent / aq. ethanol / 1 h / Heating 4: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere 5: 1.) 40percent HBr 2.) benzoyl chloride / 1.) glac.AcOH, 8 h, 20 degC 2.) DMF, 24 h, 20 degC 6: 90 percent / HBr / diethyl ether / 0.17 h 7: 88 percent / HBr / methanol / 0.17 h 8: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 9: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

1: 89 percent / 1.) boron trifluoride ether complex 2.)sodium tetrahydroborate / tetrahydrofuran / 1 h / 20 °C / nitrogen atmosphere 2: 1.) 40percent HBr 2.) benzoyl chloride / 1.) glac.AcOH, 8 h, 20 degC 2.) DMF, 24 h, 20 degC 3: 90 percent / HBr / diethyl ether / 0.17 h 4: 88 percent / HBr / methanol / 0.17 h 5: 0.044 g / bromine, iodine, triethylamine / various solvent(s) / 0.17 h / Heating 6: 0.031 g / pyridine / Heating; nitrogen atmosphere View Scheme

1: 80 percent / lead tetra acetate, acetic anhydride / 1 h 2: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 3: H2 / 10percent palladized charcoal / tetrahydrofuran / 760 Torr / Ambient temperature 4: 40 percent / trifluoroacetic acid / 2-3 deg C 70 min, CH2Cl2-CH3OH 18 deg C 2 min 5: 95 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

1: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 2: H2 / 10percent palladized charcoal / tetrahydrofuran / 760 Torr / Ambient temperature 3: 40 percent / trifluoroacetic acid / 2-3 deg C 70 min, CH2Cl2-CH3OH 18 deg C 2 min 4: 95 percent / H2 / 10percent palladized charcoal / acetic acid / 4 h / Ambient temperature 5: sodium amalgam, aq. acetic acid / 18 h / 37 °C / enzymes from Euglena gracilis 6: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min 7: 0.5 h / coproporphyrinogen-III oxidase (from Euglena gracilis) View Scheme