palladium 10 on activated carbon; hydrogen in methanol P=22502.3 Torr; 6 h;

trifluoroacetic acid in water 30 h; Heating;

trifluoroacetic acid in water 30 h; Heating;

1.1: N,N-dimethyl-formamide / 1 h / -45 °C / |Inert atmosphere 1.2: 0.5 h / -45 - 0 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 60 °C / |Inert atmosphere 3.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1.25 h / -78 °C / |Inert atmosphere 3.2: -78 - 20 °C / |Inert atmosphere 4.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / ethylene glycol dimethyl ether; water / 12 h / 60 °C / |Inert atmosphere 5.1: dimethylsulfide borane complex / tetrahydrofuran / 24 h / 0 - 20 °C 5.2: 16 h / 20 °C 6.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 48 h / 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 5 h / 0 - 45 °C 7.2: 0 - 20 °C 8.1: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 22502.3 Torr View Scheme

1.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / ethylene glycol dimethyl ether; water / 12 h / 60 °C / |Inert atmosphere 2.1: dimethylsulfide borane complex / tetrahydrofuran / 24 h / 0 - 20 °C 2.2: 16 h / 20 °C 3.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 48 h / 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 5 h / 0 - 45 °C 4.2: 0 - 20 °C 5.1: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 22502.3 Torr View Scheme

1.1: triethylamine / 2 h / 4 - 20 °C 2.1: potassium carbonate / acetonitrile / 4 h / 40 °C 3.1: potassium carbonate; water / methanol / 1 h / 20 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 110 °C 5.1: N-bromosuccinmide / N,N-dimethyl-formamide / 16 h / 20 °C 6.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / ethylene glycol dimethyl ether; water / 12 h / 60 °C / |Inert atmosphere 7.1: dimethylsulfide borane complex / tetrahydrofuran / 24 h / 0 - 20 °C 7.2: 16 h / 20 °C 8.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 48 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 5 h / 0 - 45 °C 9.2: 0 - 20 °C 10.1: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 22502.3 Torr View Scheme

1.1: potassium carbonate / acetonitrile / 4 h / 40 °C 2.1: potassium carbonate; water / methanol / 1 h / 20 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 110 °C 4.1: N-bromosuccinmide / N,N-dimethyl-formamide / 16 h / 20 °C 5.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / ethylene glycol dimethyl ether; water / 12 h / 60 °C / |Inert atmosphere 6.1: dimethylsulfide borane complex / tetrahydrofuran / 24 h / 0 - 20 °C 6.2: 16 h / 20 °C 7.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 48 h / 20 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 5 h / 0 - 45 °C 8.2: 0 - 20 °C 9.1: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 22502.3 Torr View Scheme

1.1: potassium carbonate; water / methanol / 1 h / 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 110 °C 3.1: N-bromosuccinmide / N,N-dimethyl-formamide / 16 h / 20 °C 4.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / ethylene glycol dimethyl ether; water / 12 h / 60 °C / |Inert atmosphere 5.1: dimethylsulfide borane complex / tetrahydrofuran / 24 h / 0 - 20 °C 5.2: 16 h / 20 °C 6.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 48 h / 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 5 h / 0 - 45 °C 7.2: 0 - 20 °C 8.1: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 22502.3 Torr View Scheme

1.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 110 °C 2.1: N-bromosuccinmide / N,N-dimethyl-formamide / 16 h / 20 °C 3.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / ethylene glycol dimethyl ether; water / 12 h / 60 °C / |Inert atmosphere 4.1: dimethylsulfide borane complex / tetrahydrofuran / 24 h / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 48 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 5 h / 0 - 45 °C 6.2: 0 - 20 °C 7.1: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 22502.3 Torr View Scheme

1.1: N-bromosuccinmide / N,N-dimethyl-formamide / 16 h / 20 °C 2.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / ethylene glycol dimethyl ether; water / 12 h / 60 °C / |Inert atmosphere 3.1: dimethylsulfide borane complex / tetrahydrofuran / 24 h / 0 - 20 °C 3.2: 16 h / 20 °C 4.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 48 h / 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 5 h / 0 - 45 °C 5.2: 0 - 20 °C 6.1: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 22502.3 Torr View Scheme