1: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 2: 63 percent / H2 / 10percent palladized charcoal / tetrahydrofuran / Ambient temperature 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 View Scheme

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

1: 41 percent / 1.) trifluoroacetic acid / methanol; CH2Cl2 / 1.) 2-3 deg C 70 min, 2.) 18 deg C 2 min, 20 min 2: 100 percent / H2 / 10percent palladized charcoal / acetic acid / 4 h / Ambient temperature 3: sodium amalgam, aq. acetic acid / 18 h / 37 °C / enzymes from Euglena gracilis 4: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min View Scheme

1: 78 percent / lead tetra-acetate / 1 h 2: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 3: 63 percent / H2 / 10percent palladized charcoal / tetrahydrofuran / Ambient temperature 4: 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 5: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min View Scheme

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

1: 99 percent / H2 / Adams platinum 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 View Scheme

1: 93 percent / iodine, potassium iodide 2: 99 percent / H2 / Adams platinum 3: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 4: H2 / 10percent palladized charcoal / tetrahydrofuran / 760 Torr / Ambient temperature 5: 40 percent / trifluoroacetic acid / 2-3 deg C 70 min, CH2Cl2-CH3OH 18 deg C 2 min 6: 95 percent / H2 / 10percent palladized charcoal / acetic acid / 4 h / Ambient temperature 7: sodium amalgam, aq. acetic acid / 18 h / 37 °C / enzymes from Euglena gracilis 8: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min View Scheme

1: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 2: 63 percent / H2 / 10percent palladized charcoal / tetrahydrofuran / Ambient temperature 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 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 View Scheme

1: 66 percent / toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 2: 69 percent / H2 / 10percent palladized charcoal / tetrahydrofuran 3: 41 percent / 1.) trifluoroacetic acid / methanol; CH2Cl2 / 1.) 2-3 deg C 70 min, 2.) 18 deg C 2 min, 20 min 4: 100 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 View Scheme