1: With lithium hydroxide; water in tetrahydrofuran; methanol T=22°C; 24 h; Inert atmosphere; 2: With water; citric acid in tetrahydrofuran; methanol T=0°C; Inert atmosphere;

1: With sodium t-butanolate Pinnick oxidation; 2: With sodium chlorite; 2-methyl-but-2-ene; disodium hydrogen phosphate monohydrate in tert-butyl alcohol T=20°C; Pinnick oxidation; 5 h;

1.1: tert.-butyl lithium / diethyl ether / 2.25 h / -78 - 20 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: dipyridinium dichromate / dichloromethane / 24 h / 20 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere 4.1: MgBr2*Et2O; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 4.2: 6 h / 20 °C / Inert atmosphere 5.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C / Inert atmosphere 6.1: benzene / 24 h / Inert atmosphere; Reflux 7.1: (tricyclohexylphosphine)(1,5-cyclooctadiene)pyridineiridium(I) hexafluorophosphate; hydrogen / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere 8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere 9.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 10.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 10.2: 15.75 h / 0 - 20 °C / Inert atmosphere 11.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere View Scheme

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 3.2: 15.75 h / 0 - 20 °C / Inert atmosphere 4.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere View Scheme

1.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 2.2: 15.75 h / 0 - 20 °C / Inert atmosphere 3.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere View Scheme

1.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C / Inert atmosphere 2.1: benzene / 24 h / Inert atmosphere; Reflux 3.1: (tricyclohexylphosphine)(1,5-cyclooctadiene)pyridineiridium(I) hexafluorophosphate; hydrogen / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere 4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere 5.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 6.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 6.2: 15.75 h / 0 - 20 °C / Inert atmosphere 7.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere View Scheme

1.1: (tricyclohexylphosphine)(1,5-cyclooctadiene)pyridineiridium(I) hexafluorophosphate; hydrogen / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere 3.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 4.2: 15.75 h / 0 - 20 °C / Inert atmosphere 5.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere View Scheme

1.1: tetrahydrofuran; water / 36 h / 0 - 20 °C / Inert atmosphere 2.1: MgBr2*Et2O; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.2: 6 h / 20 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C / Inert atmosphere 4.1: benzene / 24 h / Inert atmosphere; Reflux 5.1: (tricyclohexylphosphine)(1,5-cyclooctadiene)pyridineiridium(I) hexafluorophosphate; hydrogen / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere 7.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 8.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 8.2: 15.75 h / 0 - 20 °C / Inert atmosphere 9.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere View Scheme

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: potassium carbonate / tetrahydrofuran; methanol / 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 4.1: RuCl2(tricyclohexylphosphine)2(benzylidene); ethene / 20 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere 6.1: MgBr2*Et2O; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 6.2: 6 h / 20 °C / Inert atmosphere 7.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C / Inert atmosphere 8.1: benzene / 24 h / Inert atmosphere; Reflux 9.1: (tricyclohexylphosphine)(1,5-cyclooctadiene)pyridineiridium(I) hexafluorophosphate; hydrogen / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere 10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere 11.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 12.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 12.2: 15.75 h / 0 - 20 °C / Inert atmosphere 13.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere View Scheme

1.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere 2.1: MgBr2*Et2O; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.2: 6 h / 20 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C / Inert atmosphere 4.1: benzene / 24 h / Inert atmosphere; Reflux 5.1: (tricyclohexylphosphine)(1,5-cyclooctadiene)pyridineiridium(I) hexafluorophosphate; hydrogen / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere 7.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 8.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 8.2: 15.75 h / 0 - 20 °C / Inert atmosphere 9.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere View Scheme