1: With tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; Inert atmosphere; 2: With water in tetrahydrofuran

palladium 10 on activated carbon; hydrogen in ethyl acetate 48 h;

1.1: lithium chloride; N-ethyl-N,N-diisopropylamine / 1 h / 20 °C / |Inert atmosphere 1.2: 3 h / |Inert atmosphere 2.1: ozone; pyridine / dichloromethane / -78 °C 3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 3 h / -78 °C 4.1: potassium carbonate; hydrogen; RuCl2[(S)-(DM-BINAP)][(S)-DAIPEN] / isopropyl alcohol / 48 h / 7500.75 Torr / |Inert atmosphere 5.1: triethylamine; 4-(N,N-dimethlyamino)pyridine / toluene / 3 h / 150 °C / |Microwave irradiation 6.1: sec.-butyllithium; N,N,N',N,-tetramethylethylenediamine / hexane; diethyl ether / -78 °C / |Inert atmosphere 6.2: 0.53 h / -78 °C / |Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C 8.1: hydrogen; platinum(IV) oxide / ethyl acetate / 22.08 h 9.1: 2,6-dimethylpyridine / dichloromethane / 0 °C / |Inert atmosphere 10.1: sec.-butyllithium; (-)-sparteine / hexane; cyclohexane; tert-butyl methyl ether / 5 h / -78 °C / |Inert atmosphere 10.2: -78 °C / |Inert atmosphere; |Reflux 10.3: 0.5 h / 0 °C 11.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 0.5 h / 0 - 20 °C 12.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 36 h / 30 °C View Scheme