1.1: lithium diisopropyl amide 2.1: tris-(dibenzylideneacetone)dipalladium(0); di-tert-butyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine; potassium carbonate 3.1: lithium diisopropyl amide / -25 °C 4.1: sodium tetrahydroborate 5.1: triethylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 130 °C 6.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate 7.1: tetrahydrofuran / 3 h / -25 °C / |Inert atmosphere 8.1: borane-THF; sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 3 h / 0 - 20 °C / |Inert atmosphere 9.1: triethylamine; methanesulfonyl chloride / dichloromethane / 20 °C / |Inert atmosphere 9.2: 0.5 h / 20 °C / |Inert atmosphere 9.3: 3 h / |Inert atmosphere 10.1: thionyl chloride / N,N-dimethyl acetamide / 9 h / 20 °C / |Inert atmosphere 11.1: hydrogen bromide / water / 10 h / |Reflux 12.1: palladium 10 on activated carbon; hydrogen / ethanol / 12 h / 20 °C View Scheme

1.1: tris-(dibenzylideneacetone)dipalladium(0); di-tert-butyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine; potassium carbonate 2.1: lithium diisopropyl amide / -25 °C 3.1: sodium tetrahydroborate 4.1: triethylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 130 °C 5.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate 6.1: tetrahydrofuran / 3 h / -25 °C / |Inert atmosphere 7.1: borane-THF; sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 3 h / 0 - 20 °C / |Inert atmosphere 8.1: triethylamine; methanesulfonyl chloride / dichloromethane / 20 °C / |Inert atmosphere 8.2: 0.5 h / 20 °C / |Inert atmosphere 8.3: 3 h / |Inert atmosphere 9.1: thionyl chloride / N,N-dimethyl acetamide / 9 h / 20 °C / |Inert atmosphere 10.1: hydrogen bromide / water / 10 h / |Reflux 11.1: palladium 10 on activated carbon; hydrogen / ethanol / 12 h / 20 °C View Scheme

1.1: lithium diisopropyl amide / -25 °C 2.1: sodium tetrahydroborate 3.1: triethylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 130 °C 4.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate 5.1: tetrahydrofuran / 3 h / -25 °C / |Inert atmosphere 6.1: borane-THF; sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 3 h / 0 - 20 °C / |Inert atmosphere 7.1: triethylamine; methanesulfonyl chloride / dichloromethane / 20 °C / |Inert atmosphere 7.2: 0.5 h / 20 °C / |Inert atmosphere 7.3: 3 h / |Inert atmosphere 8.1: thionyl chloride / N,N-dimethyl acetamide / 9 h / 20 °C / |Inert atmosphere 9.1: hydrogen bromide / water / 10 h / |Reflux 10.1: palladium 10 on activated carbon; hydrogen / ethanol / 12 h / 20 °C View Scheme

1.1: lithium diisopropyl amide / -25 °C 2.1: sodium tetrahydroborate 3.1: triethylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 130 °C 4.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate 5.1: tetrahydrofuran / 3 h / -25 °C / |Inert atmosphere 6.1: borane-THF; sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 3 h / 0 - 20 °C / |Inert atmosphere 7.1: triethylamine; methanesulfonyl chloride / dichloromethane / 20 °C / |Inert atmosphere 7.2: 0.5 h / 20 °C / |Inert atmosphere 7.3: 3 h / |Inert atmosphere 8.1: thionyl chloride / N,N-dimethyl acetamide / 9 h / 20 °C / |Inert atmosphere 9.1: hydrogen bromide / water / 10 h / |Reflux 10.1: palladium 10 on activated carbon; hydrogen / ethanol / 12 h / 20 °C View Scheme

1.1: tetrahydrofuran / 3 h / -25 °C / |Inert atmosphere 2.1: borane-THF; sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 3 h / 0 - 20 °C / |Inert atmosphere 3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 20 °C / |Inert atmosphere 3.2: 0.5 h / 20 °C / |Inert atmosphere 3.3: 3 h / |Inert atmosphere 4.1: thionyl chloride / N,N-dimethyl acetamide / 9 h / 20 °C / |Inert atmosphere 5.1: hydrogen bromide / water / 10 h / |Reflux 6.1: palladium 10 on activated carbon; hydrogen / ethanol / 12 h / 20 °C View Scheme

1.1: sodium tetrahydroborate 2.1: triethylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 130 °C 3.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate 4.1: tetrahydrofuran / 3 h / -25 °C / |Inert atmosphere 5.1: borane-THF; sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 3 h / 0 - 20 °C / |Inert atmosphere 6.1: triethylamine; methanesulfonyl chloride / dichloromethane / 20 °C / |Inert atmosphere 6.2: 0.5 h / 20 °C / |Inert atmosphere 6.3: 3 h / |Inert atmosphere 7.1: thionyl chloride / N,N-dimethyl acetamide / 9 h / 20 °C / |Inert atmosphere 8.1: hydrogen bromide / water / 10 h / |Reflux 9.1: palladium 10 on activated carbon; hydrogen / ethanol / 12 h / 20 °C View Scheme

palladium on activated charcoal T=300°C; the structure was confirmed; Product distribution;