lithium hydroxide in tetrahydrofuran; methanol; water T=50°C; 1 h;

hydrogen; palladium on activated charcoal in methanol P=3102.9 Torr; 1 h;

1: 60 percent / Cu, i-Pr2NEt, DMF / various solvent(s) / 130 °C 2: Et3SiH-trifluoroacetic acid / CH2Cl2 / 0 - 20 °C 3: acetic acid 4: 68 percent / MeC(CH2OH)3, KOH / methanol 5: 75 percent / 0.01 M aq. KOH / aq. KOH View Scheme

1: 90 percent / hydrogenolysis 2: 60 percent / Cu, i-Pr2NEt, DMF / various solvent(s) / 130 °C 3: Et3SiH-trifluoroacetic acid / CH2Cl2 / 0 - 20 °C 4: acetic acid 5: 68 percent / MeC(CH2OH)3, KOH / methanol 6: 75 percent / 0.01 M aq. KOH / aq. KOH View Scheme

1: 90 percent / Al-Hg / tetrahydrofuran 2: 90 percent / hydrogenolysis 3: 60 percent / Cu, i-Pr2NEt, DMF / various solvent(s) / 130 °C 4: Et3SiH-trifluoroacetic acid / CH2Cl2 / 0 - 20 °C 5: acetic acid 6: 68 percent / MeC(CH2OH)3, KOH / methanol 7: 75 percent / 0.01 M aq. KOH / aq. KOH View Scheme

1: 81 percent / 1.) H2O2, BF3*Et2O / 3.) DMAP / 1.) CH2Cl2; 2.) CH2Cl2, 8 min, 23 deg C; 3.) CH2Cl2, 23 deg C, 18 h 2: 96 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 50 °C View Scheme

1: 76 percent / tetrahydrofuran / 0.33 h / 22 °C 2: 81 percent / 1.) H2O2, BF3*Et2O / 3.) DMAP / 1.) CH2Cl2; 2.) CH2Cl2, 8 min, 23 deg C; 3.) CH2Cl2, 23 deg C, 18 h 3: 96 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 50 °C View Scheme

1: 65 percent / MnO2 / CH2Cl2 / 23 h / 24 °C 2: 98 percent / NaOMe / methanol / 1.25 h / 0 °C 3: xylene / 5 h / Heating; variation of time 4: 85 percent / anhydrous HCl / methanol / 12 h / 70 °C 5: 76 percent / tetrahydrofuran / 0.33 h / 22 °C 6: 81 percent / 1.) H2O2, BF3*Et2O / 3.) DMAP / 1.) CH2Cl2; 2.) CH2Cl2, 8 min, 23 deg C; 3.) CH2Cl2, 23 deg C, 18 h 7: 96 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 50 °C View Scheme

1: 98 percent / NaOMe / methanol / 1.25 h / 0 °C 2: xylene / 5 h / Heating; variation of time 3: 85 percent / anhydrous HCl / methanol / 12 h / 70 °C 4: 76 percent / tetrahydrofuran / 0.33 h / 22 °C 5: 81 percent / 1.) H2O2, BF3*Et2O / 3.) DMAP / 1.) CH2Cl2; 2.) CH2Cl2, 8 min, 23 deg C; 3.) CH2Cl2, 23 deg C, 18 h 6: 96 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 50 °C View Scheme

1: 96 percent / AcOH / tetrahydrofuran; H2O / 24 h / 24 °C 2: 65 percent / MnO2 / CH2Cl2 / 23 h / 24 °C 3: 98 percent / NaOMe / methanol / 1.25 h / 0 °C 4: xylene / 5 h / Heating; variation of time 5: 85 percent / anhydrous HCl / methanol / 12 h / 70 °C 6: 76 percent / tetrahydrofuran / 0.33 h / 22 °C 7: 81 percent / 1.) H2O2, BF3*Et2O / 3.) DMAP / 1.) CH2Cl2; 2.) CH2Cl2, 8 min, 23 deg C; 3.) CH2Cl2, 23 deg C, 18 h 8: 96 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 50 °C View Scheme