1.1: diisobutylaluminium hydride / tetrahydrofuran / 5.25 h / 0 - 20 °C 2.1: tin tetrabromide / dichloromethane / 0.08 h / -78 °C 2.2: 0.5 h / -78 °C 3.1: pyridine / dichloromethane / 16 h 4.1: tri-n-butyl-tin hydride; 2,2'-azo-bisisobutyronitrile / toluene / 1.5 h / |Inert atmosphere; |Reflux 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane 6.1: pyridine / 5 h 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C 8.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 9.1: diethyl ether / 1 h / -78 °C 10.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 11.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 11.2: 15 h / 20 °C 12.1: diisobutylaluminium hydride / tetrahydrofuran / 3.25 h / 0 - 20 °C 13.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 14.1: lithium diisopropyl amide; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 40 °C 14.2: 0.03 h / -78 °C 15.1: 2,6-dimethylpyridine / dichloromethane / 6 h / 0 °C 16.1: dichloro-acetic acid / dichloromethane / 2 h / 20 °C 17.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 18.1: sodium chlorite; sodium dihydrogenphosphate; 1,1,2,2-tetramethylethylene / tetrahydrofuran; water; tert-butyl alcohol / 1 h / 20 °C 19.1: potassium carbonate; MgBr2(Et2O); butane-1-thiol / diethyl ether / 2 h / 20 °C 20.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.75 h / 0 °C 20.2: 5 h / 75 °C 21.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C 22.1: 3,3-dimethyldioxirane / dichloromethane; acetone / -50 °C View Scheme

1.1: diisobutylaluminium hydride / tetrahydrofuran / 5.25 h / 0 - 20 °C 2.1: tin tetrabromide / dichloromethane / 0.08 h / -78 °C 2.2: 0.5 h / -78 °C 3.1: pyridine / dichloromethane / 16 h 4.1: tri-n-butyl-tin hydride; 2,2'-azo-bisisobutyronitrile / toluene / 1.5 h / |Inert atmosphere; |Reflux 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane 6.1: pyridine / 5 h 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C 8.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 9.1: diethyl ether / 1 h / -78 °C 10.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 11.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 11.2: 15 h / 20 °C 12.1: diisobutylaluminium hydride / tetrahydrofuran / 3.25 h / 0 - 20 °C 13.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 14.1: lithium diisopropyl amide; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 40 °C 14.2: 0.03 h / -78 °C 15.1: 2,6-dimethylpyridine / dichloromethane / 6 h / 0 °C 16.1: dichloro-acetic acid / dichloromethane / 2 h / 20 °C 17.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 18.1: sodium chlorite; sodium dihydrogenphosphate; 1,1,2,2-tetramethylethylene / tetrahydrofuran; water; tert-butyl alcohol / 1 h / 20 °C 19.1: potassium carbonate; MgBr2(Et2O); butane-1-thiol / diethyl ether / 2 h / 20 °C 20.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.75 h / 0 °C 20.2: 5 h / 75 °C 21.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C View Scheme