Streptomyces hygroscopicus var. limoneus in water T=28°C; 168 h; Further byproducts.;

Streptomyces hygroscopicus var. limoneus in water T=28°C; 168 h; Further byproducts.;

ammonia; sodium in tetrahydrofuran T=-78°C; 6 h;

1: 75 percent / propan-2-ol / 110 h / 120 °C 2: 89 percent / sodium hydride, di-imidazolyl sulphone / dimethylformamide / 1.5 h / 50 °C 3: 91 percent / propan-2-ol / 4 h / 80 °C 4: 75 percent / H2 / Ranei nickel T-4 / dioxane; ethanol / 6 h / 60 °C 5: 86 percent / aq. 80percent acetic acid / 9 h / 50 °C 6: 61 percent / imidazole / CHCl3 / 48 h / Heating 7: 84 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 10 h / Ambient temperature 8: liquid ammonia, sodium / tetrahydrofuran / 6 h / -78 °C View Scheme

1: 75 percent / propan-2-ol / 110 h / 120 °C 2: 89 percent / sodium hydride, di-imidazolyl sulphone / dimethylformamide / 1.5 h / 50 °C 3: 91 percent / propan-2-ol / 4 h / 80 °C 4: 75 percent / H2 / Ranei nickel T-4 / dioxane; ethanol / 6 h / 60 °C 5: 86 percent / aq. 80percent acetic acid / 9 h / 50 °C 6: 61 percent / imidazole / CHCl3 / 48 h / Heating 7: 84 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 10 h / Ambient temperature 8: liquid ammonia, sodium / tetrahydrofuran / 6 h / -78 °C View Scheme

1: 91 percent / propan-2-ol / 4 h / 80 °C 2: 75 percent / H2 / Ranei nickel T-4 / dioxane; ethanol / 6 h / 60 °C 3: 86 percent / aq. 80percent acetic acid / 9 h / 50 °C 4: 61 percent / imidazole / CHCl3 / 48 h / Heating 5: 84 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 10 h / Ambient temperature 6: liquid ammonia, sodium / tetrahydrofuran / 6 h / -78 °C View Scheme

1: 89 percent / sodium hydride, di-imidazolyl sulphone / dimethylformamide / 1.5 h / 50 °C 2: 91 percent / propan-2-ol / 4 h / 80 °C 3: 75 percent / H2 / Ranei nickel T-4 / dioxane; ethanol / 6 h / 60 °C 4: 86 percent / aq. 80percent acetic acid / 9 h / 50 °C 5: 61 percent / imidazole / CHCl3 / 48 h / Heating 6: 84 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 10 h / Ambient temperature 7: liquid ammonia, sodium / tetrahydrofuran / 6 h / -78 °C View Scheme

1: 75 percent / H2 / Ranei nickel T-4 / dioxane; ethanol / 6 h / 60 °C 2: 86 percent / aq. 80percent acetic acid / 9 h / 50 °C 3: 61 percent / imidazole / CHCl3 / 48 h / Heating 4: 84 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 10 h / Ambient temperature 5: liquid ammonia, sodium / tetrahydrofuran / 6 h / -78 °C View Scheme

1: 55.7 percent / imidazole / CHCl3 / 40 h / Heating 2: 74.2 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 4.5 h / Ambient temperature 3: 1) sodium, 2) ammonium chloride / 1) liq NH3, THF, -70 deg C, 4 h 20 min, 2) room temp., 4.5 h View Scheme

1: 74.2 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 4.5 h / Ambient temperature 2: 1) sodium, 2) ammonium chloride / 1) liq NH3, THF, -70 deg C, 4 h 20 min, 2) room temp., 4.5 h View Scheme