1: DIBAL / CH2Cl2 2: imidazole / dimethylformamide / 10 h / 55 °C 3: 61 percent / CuBr / chlorobenzene / 4 h / 115 °C 4: 96 percent / aq. NaOH / methanol; tetrahydrofuran 5: 93 percent / Li, NH3 / tetrahydrofuran / 2 h / -78 °C 6: 1.) n-BuLi, ClPO(NMe2)2, 2.) Li, EtNH2 / 1.) THF, HMPA, 2.) THF, t-BuOH, 0 deg C, 3 h 7: 95 percent / (n-Bu)4NF / tetrahydrofuran / 12 h / 55 °C View Scheme

1: 96 percent / aq. NaOH / methanol; tetrahydrofuran 2: 93 percent / Li, NH3 / tetrahydrofuran / 2 h / -78 °C 3: 1.) n-BuLi, ClPO(NMe2)2, 2.) Li, EtNH2 / 1.) THF, HMPA, 2.) THF, t-BuOH, 0 deg C, 3 h 4: 95 percent / (n-Bu)4NF / tetrahydrofuran / 12 h / 55 °C View Scheme

Triton X-100 in phosphate buffer T=23°C; 48 h;

potassium hydroxide in diethylene glycol 2 h; Heating;

1.1: 6 percent / sodium / 2-methyl-propan-2-ol; toluene / 22 h / Heating 2.1: 100 percent / pyridine; 4-(dimethylamino)pyridine / 20 °C 3.1: 79 percent / lithium triethylborohydride / dimethylsulfoxide / 1 h / 65 °C 4.1: 93 percent / H2 / Pd/C / CH2Cl2; methanol / 20 °C 5.1: pyridine / 5 h / Heating 6.1: 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 20 °C 7.1: 69 percent / HCl / acetone; methanol / 2 h / 60 °C 8.1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C 9.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 10.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 10.2: 77 percent / KOH / 2 h / Heating View Scheme

1.1: 100 percent / pyridine; 4-(dimethylamino)pyridine / 20 °C 2.1: 79 percent / lithium triethylborohydride / dimethylsulfoxide / 1 h / 65 °C 3.1: 93 percent / H2 / Pd/C / CH2Cl2; methanol / 20 °C 4.1: pyridine / 5 h / Heating 5.1: 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 20 °C 6.1: 69 percent / HCl / acetone; methanol / 2 h / 60 °C 7.1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C 8.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 9.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 9.2: 77 percent / KOH / 2 h / Heating View Scheme

1.1: 93 percent / H2 / Pd/C / CH2Cl2; methanol / 20 °C 2.1: pyridine / 5 h / Heating 3.1: 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 20 °C 4.1: 69 percent / HCl / acetone; methanol / 2 h / 60 °C 5.1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C 6.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 7.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 7.2: 77 percent / KOH / 2 h / Heating View Scheme

1.1: 79 percent / lithium triethylborohydride / dimethylsulfoxide / 1 h / 65 °C 2.1: 93 percent / H2 / Pd/C / CH2Cl2; methanol / 20 °C 3.1: pyridine / 5 h / Heating 4.1: 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 20 °C 5.1: 69 percent / HCl / acetone; methanol / 2 h / 60 °C 6.1: 95 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C 7.1: 77 percent / NaOH / methanol; tetrahydrofuran / 3 h / 20 °C 8.1: NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether; ethanol / 1 h / Heating; Huang-Minlon reduction 8.2: 77 percent / KOH / 2 h / Heating View Scheme

lithium; ethylenediamine 2 h; Heating;

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