lithium hydroxide in tetrahydrofuran T=20°C; Hydrolysis;

1: With tetrabutyl ammonium fluoride in tetrahydrofuran 2: With lithium hydroxide in tetrahydrofuran; water T=20°C; Further stages.;

1: 89 percent / NaN(SiMe3)2 / tetrahydrofuran / 2 h / -80 - 20 °C 2: 92 percent / NH4F / tetrahydrofuran; methanol / 4 h 3: 97 percent / pyridine / 1 h / 20 °C 4: 83 percent / 3 percent HCl in MeOH / diethyl ether / 20 °C 5: periodinane / CH2Cl2 / 2 h / 20 °C 6: 75 percent / NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / 20 °C 7: 85 percent / (S)-BINAL-H / 2 h / -100 °C 8: 1N aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

1: 93 percent / DIBAL-H / toluene / 0.5 h / -80 °C 2: 89 percent / NaN(SiMe3)2 / tetrahydrofuran / 2 h / -80 - 20 °C 3: 92 percent / NH4F / tetrahydrofuran; methanol / 4 h 4: 97 percent / pyridine / 1 h / 20 °C 5: 83 percent / 3 percent HCl in MeOH / diethyl ether / 20 °C 6: periodinane / CH2Cl2 / 2 h / 20 °C 7: 75 percent / NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / 20 °C 8: 85 percent / (S)-BINAL-H / 2 h / -100 °C 9: 1N aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

1: 75 percent / NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / 20 °C 2: 85 percent / (S)-BINAL-H / 2 h / -100 °C 3: 1N aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

1: periodinane / CH2Cl2 / 2 h / 20 °C 2: 75 percent / NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / 20 °C 3: 85 percent / (S)-BINAL-H / 2 h / -100 °C 4: 1N aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

1: 97 percent / pyridine / 1 h / 20 °C 2: 83 percent / 3 percent HCl in MeOH / diethyl ether / 20 °C 3: periodinane / CH2Cl2 / 2 h / 20 °C 4: 75 percent / NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / 20 °C 5: 85 percent / (S)-BINAL-H / 2 h / -100 °C 6: 1N aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

1: 85 percent / (S)-BINAL-H / 2 h / -100 °C 2: 1N aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

1: 83 percent / 3 percent HCl in MeOH / diethyl ether / 20 °C 2: periodinane / CH2Cl2 / 2 h / 20 °C 3: 75 percent / NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / 20 °C 4: 85 percent / (S)-BINAL-H / 2 h / -100 °C 5: 1N aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

1: 92 percent / NH4F / tetrahydrofuran; methanol / 4 h 2: 97 percent / pyridine / 1 h / 20 °C 3: 83 percent / 3 percent HCl in MeOH / diethyl ether / 20 °C 4: periodinane / CH2Cl2 / 2 h / 20 °C 5: 75 percent / NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / 20 °C 6: 85 percent / (S)-BINAL-H / 2 h / -100 °C 7: 1N aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme