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: trifluorormethanesulfonic acid; acetic anhydride; acetic acid / 1 h / 20 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol; dichloromethane / 1.33 h / 20 °C / Inert atmosphere View Scheme

1.1: toluene-4-sulfonic acid / dichloromethane / 16 h / 20 °C / Darkness 1.2: 10 h 1.3: 14 h / Darkness 2.1: zinc diacetate / methanol; dichloromethane / 2 h / Darkness 3.1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / 72 h / Darkness 3.2: 14 h / Darkness 4.1: hydrogenchloride; water / 6 h / 20 °C 5.1: sodium amalgam; potassium hydroxide / 0.08 h / 80 °C / Darkness 6.1: recombinant oxygen-independent coproporphyrinogen III oxidase; [14C]-Ademetionine; Reduced nicotinamide-adenine dinucleotide; threo-1,4-dimercapto-2,3-butanediol / 1 h / 37 °C / pH 7 / Inert atmosphere; Bis-Tris buffer; Enzymatic reaction 6.2: 0.25 h / Bis-Tris buffer 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 View Scheme

Multi-step reaction with 2 steps 1: H2 / Pd/C2: TFA  

Multi-step reaction with 3 steps 1: 81.5 percent / acetic acid; H2O / 1 h / Heating2: 99 percent / H2 / 10percent Pd/C / tetrahydrofuran3: 60 percent / trimethyl orthoformate / trifluoroacetic acid / 0.37 h / 0 °C