sodium periodate; osmium(VIII) oxide in tetrahydrofuran; water

hydrogen; palladium on activated charcoal in benzene

hydrogen; palladium on activated charcoal P=3102.89 Torr;

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h 1.2: 90 percent / tetrahydrofuran; hexane / 24 h 2.1: 55 percent / NaIO4 / OsO4 / tetrahydrofuran; H2O View Scheme

1.1: 95 percent / tetramethylammonium hydroxide pentahydrate / acetonitrile / 48 h / 20 °C 2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h 2.2: 90 percent / tetrahydrofuran; hexane / 24 h 3.1: 55 percent / NaIO4 / OsO4 / tetrahydrofuran; H2O View Scheme

1: 99 percent / N-methylmorpholine oxide / OsO4 / tetrahydrofuran; H2O; 2-methyl-propan-2-ol 2: 75 percent / NaIO4/silica gel / CH2Cl2 / 0.33 h 3: 80 percent / hydrogen / Pd/C / benzene View Scheme

1: 75 percent / NaIO4/silica gel / CH2Cl2 / 0.33 h 2: 80 percent / hydrogen / Pd/C / benzene View Scheme

1.1: 95 percent / tetramethylammonium hydroxide pentahydrate / acetonitrile / 48 h / 20 °C 2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h 2.2: 90 percent / tetrahydrofuran; hexane / 24 h 3.1: 55 percent / NaIO4 / OsO4 / tetrahydrofuran; H2O View Scheme