1: 86 percent / sodium benzyl oxide / phenylmethanol / 209 °C 2: 70 percent 3: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 4: 63 percent / H2 / 10percent palladized charcoal / tetrahydrofuran / Ambient temperature 5: 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 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

1: 86 percent / sodium benzyl oxide / phenylmethanol / 209 °C 2: 70 percent 3: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 4: 63 percent / H2 / 10percent palladized charcoal / tetrahydrofuran / Ambient temperature 5: 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 6: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min View Scheme