1: H2; K2CO3 / Pd/C / ethanol / 20 °C / 4654.33 Torr 2: NaBH4; aq. NaOH / ethanol / 6 h / -10 °C 3: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C 4: 80 percent / Ph2PH; n-BuLi / tetrahydrofuran; hexane / 20 h / Heating 5: 100 percent / K2CO3; tetrabutylammonium bromide / acetone / 8 h / Heating 6: 83 percent / aq. KOH / methanol / 3 h / Heating View Scheme

1.1: potassium carbonate / acetone / 4 h / 40 °C 2.1: triethylamine; zinc trifluoromethanesulfonate; (1S,2R)-(+)-N-methylephedrine / toluene / 20 °C 2.2: 16 h / 20 °C 3.1: 4-(N,N-dimethlyamino)pyridine; 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere 4.1: ethylene glycol dimethyl ether / 6.5 h / 20 - 65 °C / Inert atmosphere 5.1: potassium carbonate; hydrogen / palladium on activated charcoal / water; methanol / 16 h / 20 °C 6.1: sodium hydroxide / water; methanol / 0.5 h / -5 °C 6.2: 18 h / -5 - 20 °C 6.3: pH 2 - 3 View Scheme

1: decalin / 7 h / 217 °C / Inert atmosphere 2: potassium carbonate; sodium iodide / acetone / 4 h / Reflux 3: n-butyllithium / hexane; tetrahydrofuran / Cooling 4: pyridinium chlorochromate / dichloromethane / 20 °C 5: dimethylsulfide borane complex; (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / toluene; tetrahydrofuran / -30 - -25 °C 6: 1H-imidazole / dichloromethane / 20 °C 7: dichloromethane / 20 °C / Inert atmosphere 8: potassium carbonate; hydrogen / palladium 10 on activated carbon / ethanol / 20 °C 9: sodium hydroxide; water; sodium tetrahydroborate / ethanol 10: hydrogen / palladium 10 on activated carbon / acetic acid 11: potassium carbonate; tetra-(n-butyl)ammonium iodide / ethanol / 20 °C / Reflux 12: sodium hydroxide / ethanol; water View Scheme

1: potassium carbonate; sodium iodide / ethanol / 3 h / Reflux 2: decalin / 7 h / 217 °C / Inert atmosphere 3: potassium carbonate; sodium iodide / acetone / 4 h / Reflux 4: n-butyllithium / hexane; tetrahydrofuran / Cooling 5: pyridinium chlorochromate / dichloromethane / 20 °C 6: dimethylsulfide borane complex; (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / toluene; tetrahydrofuran / -30 - -25 °C 7: 1H-imidazole / dichloromethane / 20 °C 8: dichloromethane / 20 °C / Inert atmosphere 9: potassium carbonate; hydrogen / palladium 10 on activated carbon / ethanol / 20 °C 10: sodium hydroxide; water; sodium tetrahydroborate / ethanol 11: hydrogen / palladium 10 on activated carbon / acetic acid 12: potassium carbonate; tetra-(n-butyl)ammonium iodide / ethanol / 20 °C / Reflux 13: sodium hydroxide / ethanol; water View Scheme

1: pyridinium chlorochromate / dichloromethane / 20 °C 2: dimethylsulfide borane complex; (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / toluene; tetrahydrofuran / -30 - -25 °C 3: 1H-imidazole / dichloromethane / 20 °C 4: dichloromethane / 20 °C / Inert atmosphere 5: potassium carbonate; hydrogen / palladium 10 on activated carbon / ethanol / 20 °C 6: sodium hydroxide; water; sodium tetrahydroborate / ethanol 7: hydrogen / palladium 10 on activated carbon / acetic acid 8: potassium carbonate; tetra-(n-butyl)ammonium iodide / ethanol / 20 °C / Reflux 9: sodium hydroxide / ethanol; water View Scheme

1: potassium carbonate; hydrogen / palladium 10 on activated carbon / ethanol / 20 °C 2: sodium hydroxide; water; sodium tetrahydroborate / ethanol 3: hydrogen / palladium 10 on activated carbon / acetic acid 4: potassium carbonate; tetra-(n-butyl)ammonium iodide / ethanol / 20 °C / Reflux 5: sodium hydroxide / ethanol; water View Scheme

1: hydrogen / palladium 10 on activated carbon / acetic acid 2: potassium carbonate; tetra-(n-butyl)ammonium iodide / ethanol / 20 °C / Reflux 3: sodium hydroxide / ethanol; water View Scheme

1: n-butyllithium / hexane; tetrahydrofuran / Cooling 2: pyridinium chlorochromate / dichloromethane / 20 °C 3: dimethylsulfide borane complex; (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole / toluene; tetrahydrofuran / -30 - -25 °C 4: 1H-imidazole / dichloromethane / 20 °C 5: dichloromethane / 20 °C / Inert atmosphere 6: potassium carbonate; hydrogen / palladium 10 on activated carbon / ethanol / 20 °C 7: sodium hydroxide; water; sodium tetrahydroborate / ethanol 8: hydrogen / palladium 10 on activated carbon / acetic acid 9: potassium carbonate; tetra-(n-butyl)ammonium iodide / ethanol / 20 °C / Reflux 10: sodium hydroxide / ethanol; water View Scheme

1.1: triethylamine; zinc trifluoromethanesulfonate; (1S,2R)-(+)-N-methylephedrine / toluene / 20 °C 1.2: 16 h / 20 °C 2.1: 4-(N,N-dimethlyamino)pyridine; 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere 3.1: ethylene glycol dimethyl ether / 6.5 h / 20 - 65 °C / Inert atmosphere 4.1: potassium carbonate; hydrogen / palladium on activated charcoal / water; methanol / 16 h / 20 °C 5.1: sodium hydroxide / water; methanol / 0.5 h / -5 °C 5.2: 18 h / -5 - 20 °C 5.3: pH 2 - 3 View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere 2.1: ethylene glycol dimethyl ether / 6.5 h / 20 - 65 °C / Inert atmosphere 3.1: potassium carbonate; hydrogen / palladium on activated charcoal / water; methanol / 16 h / 20 °C 4.1: sodium hydroxide / water; methanol / 0.5 h / -5 °C 4.2: 18 h / -5 - 20 °C 4.3: pH 2 - 3 View Scheme