potassium hydroxide in ethylene glycol dimethyl ether Hydrolysis; 12 h; reflux;

1.1: 90 percent / KOH; I2 / dimethylformamide / 2 h / 25 °C 2.1: 88 percent / TEA / DMAP / acetonitrile / 3 h 3.1: 77 percent / Et3N; Bu4NI / PdCl2(dppf) / dimethylformamide; H2O / 2 h / 50 °C 4.1: 100 percent / NaOMe / methanol / 1 h / 25 °C 5.1: 85 percent / NaBH4; NiCl2*6H2O / methanol / 6 h / 25 °C 6.1: 95 percent / NaOH 6N / tetrahydrofuran / 6 h / 25 °C 7.1: TEA / acetone / 0 °C 7.2: 95 percent / NaN3 / acetone / 0 °C 8.1: 95 percent / 0.17 h / 115 °C 9.1: 95 percent / NaOMe / methanol / 25 °C 10.1: 95 percent / KOH 6N / 1,2-dimethoxy-ethane / 12 h / reflux View Scheme

1.1: 88 percent / TEA / DMAP / acetonitrile / 3 h 2.1: 77 percent / Et3N; Bu4NI / PdCl2(dppf) / dimethylformamide; H2O / 2 h / 50 °C 3.1: 100 percent / NaOMe / methanol / 1 h / 25 °C 4.1: 85 percent / NaBH4; NiCl2*6H2O / methanol / 6 h / 25 °C 5.1: 95 percent / NaOH 6N / tetrahydrofuran / 6 h / 25 °C 6.1: TEA / acetone / 0 °C 6.2: 95 percent / NaN3 / acetone / 0 °C 7.1: 95 percent / 0.17 h / 115 °C 8.1: 95 percent / NaOMe / methanol / 25 °C 9.1: 95 percent / KOH 6N / 1,2-dimethoxy-ethane / 12 h / reflux View Scheme

1.1: 77 percent / Et3N; Bu4NI / PdCl2(dppf) / dimethylformamide; H2O / 2 h / 50 °C 2.1: 100 percent / NaOMe / methanol / 1 h / 25 °C 3.1: 85 percent / NaBH4; NiCl2*6H2O / methanol / 6 h / 25 °C 4.1: 95 percent / NaOH 6N / tetrahydrofuran / 6 h / 25 °C 5.1: TEA / acetone / 0 °C 5.2: 95 percent / NaN3 / acetone / 0 °C 6.1: 95 percent / 0.17 h / 115 °C 7.1: 95 percent / NaOMe / methanol / 25 °C 8.1: 95 percent / KOH 6N / 1,2-dimethoxy-ethane / 12 h / reflux View Scheme

hydrogenchloride; water

1: platinum; decalin 2: water; HCl View Scheme

1: aqueous ethanol 2: platinum / Hydrogenation 3: water; HCl View Scheme

1: H2O 2: platinum; acetic acid anhydride / Hydrogenation 3: platinum; decalin 4: water; HCl View Scheme

1: platinum; acetic acid anhydride / Hydrogenation 2: platinum; decalin 3: water; HCl View Scheme

1: platinum / Hydrogenation 2: water; HCl View Scheme