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

acetic acid; zinc T=65°C;

acetic acid; sodium nitrite anschliessend Erhitzen mit 4-Acetyl-5-oxo-hexansaeure-methylester und Zink-Pulver;

methanol; sodium

1: sodium / 100 °C / 13 Torr 2: methanol; sodium View Scheme

1: sodium / 100 °C / 13 Torr 2: methanol; sodium 3: sodium / 100 °C / 13 Torr 4: methanol; sodium View Scheme

1: methanol; sodium 2: sodium / 100 °C / 13 Torr 3: methanol; sodium 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: H2 / Pd/C / ethanol / 2 h / 20 °C 2: TFA / 1 h / Heating 3: TFA / 1 h / Heating View Scheme

1.1: bromine / tert-butyl methyl ether / 20 °C / Inert atmosphere 2.1: hydrogenchloride / methanol; water / 11 h / 50 °C 3.1: 10 palladium on activated carbon; hydrogen / tetrahydrofuran / 3 h / 20 °C / 750.08 Torr 4.1: trifluoroacetic acid / 1.17 h / 0 °C / Inert atmosphere 4.2: 0 - 5 °C / Inert atmosphere 5.1: trifluorormethanesulfonic acid; acetic anhydride; acetic acid / 1 h / 20 °C / Inert atmosphere 6.1: sodium tetrahydroborate / methanol; dichloromethane / 1.33 h / 20 °C / Inert atmosphere View Scheme