in dichloromethane T=20 - 50°C;

potassium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; dihydrogen peroxide 1.) THF, -30 deg C to RT, 2.) H2O, 45 deg C, 4 h, 3.) MeOH, reflux, 5 h; Yield given. Multistep reaction;

sodium cyanoborohydride; acetic acid in methanol T=20°C; 1 h; Inert atmosphere; Overall yield = 168.3 mg;

1.1: hydrazine hydrate / tetrahydrofuran / 1 h / 0 °C 2.1: hydrogenchloride; tert.-butylnitrite / ethyl acetate; isopropyl alcohol / 1 h / 60 °C / |Inert atmosphere 3.1: titanium tetrachloride; triethylsilane / dichloromethane / 1 h / 0 °C / |Inert atmosphere 4.1: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 80 °C / |Inert atmosphere 5.1: sodium hydrogencarbonate / dichloromethane; water / 8 h / 20 °C 6.1: Grubb's 2nd generation catalyst / toluene / 1 h / 80 °C / |Inert atmosphere 7.1: tetrakis(triphenylphosphine) palladium(0); silver carbonate / toluene / 4 h / 100 °C / |Inert atmosphere 8.1: methanol; magnesium / benzene / 1 h / 20 °C / |Inert atmosphere 9.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1 h / 20 °C / |Inert atmosphere 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 11.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / |Inert atmosphere 12.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C 13.1: diethyl ether; methanol / 0.25 h / 20 °C / |Inert atmosphere 14.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / |Inert atmosphere 15.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 15.2: 0.5 h / 50 °C / |Inert atmosphere 16.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / |Inert atmosphere View Scheme

1.1: hydrogenchloride; tert.-butylnitrite / ethyl acetate; isopropyl alcohol / 1 h / 60 °C / |Inert atmosphere 2.1: titanium tetrachloride; triethylsilane / dichloromethane / 1 h / 0 °C / |Inert atmosphere 3.1: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 80 °C / |Inert atmosphere 4.1: sodium hydrogencarbonate / dichloromethane; water / 8 h / 20 °C 5.1: Grubb's 2nd generation catalyst / toluene / 1 h / 80 °C / |Inert atmosphere 6.1: tetrakis(triphenylphosphine) palladium(0); silver carbonate / toluene / 4 h / 100 °C / |Inert atmosphere 7.1: methanol; magnesium / benzene / 1 h / 20 °C / |Inert atmosphere 8.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1 h / 20 °C / |Inert atmosphere 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 10.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / |Inert atmosphere 11.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C 12.1: diethyl ether; methanol / 0.25 h / 20 °C / |Inert atmosphere 13.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / |Inert atmosphere 14.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 14.2: 0.5 h / 50 °C / |Inert atmosphere 15.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / |Inert atmosphere View Scheme

1.1: N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere 1.2: 2 h / -78 - 0 °C / |Inert atmosphere 2.1: hydrazine hydrate / tetrahydrofuran / 1 h / 0 °C 3.1: hydrogenchloride; tert.-butylnitrite / ethyl acetate; isopropyl alcohol / 1 h / 60 °C / |Inert atmosphere 4.1: titanium tetrachloride; triethylsilane / dichloromethane / 1 h / 0 °C / |Inert atmosphere 5.1: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 80 °C / |Inert atmosphere 6.1: sodium hydrogencarbonate / dichloromethane; water / 8 h / 20 °C 7.1: Grubb's 2nd generation catalyst / toluene / 1 h / 80 °C / |Inert atmosphere 8.1: tetrakis(triphenylphosphine) palladium(0); silver carbonate / toluene / 4 h / 100 °C / |Inert atmosphere 9.1: methanol; magnesium / benzene / 1 h / 20 °C / |Inert atmosphere 10.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1 h / 20 °C / |Inert atmosphere 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 12.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / |Inert atmosphere 13.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C 14.1: diethyl ether; methanol / 0.25 h / 20 °C / |Inert atmosphere 15.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / |Inert atmosphere 16.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 16.2: 0.5 h / 50 °C / |Inert atmosphere 17.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / |Inert atmosphere View Scheme

1.1: titanium tetrachloride; triethylsilane / dichloromethane / 1 h / 0 °C / |Inert atmosphere 2.1: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 80 °C / |Inert atmosphere 3.1: sodium hydrogencarbonate / dichloromethane; water / 8 h / 20 °C 4.1: Grubb's 2nd generation catalyst / toluene / 1 h / 80 °C / |Inert atmosphere 5.1: tetrakis(triphenylphosphine) palladium(0); silver carbonate / toluene / 4 h / 100 °C / |Inert atmosphere 6.1: methanol; magnesium / benzene / 1 h / 20 °C / |Inert atmosphere 7.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1 h / 20 °C / |Inert atmosphere 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 9.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / |Inert atmosphere 10.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C 11.1: diethyl ether; methanol / 0.25 h / 20 °C / |Inert atmosphere 12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / |Inert atmosphere 13.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 13.2: 0.5 h / 50 °C / |Inert atmosphere 14.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / |Inert atmosphere View Scheme

1.1: [bis(acetoxy)iodo]benzene / toluene / 1 h / 60 °C / |Inert atmosphere 2.1: titanium tetrachloride; triethylsilane / dichloromethane / 1 h / 0 °C / |Inert atmosphere 3.1: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 80 °C / |Inert atmosphere 4.1: sodium hydrogencarbonate / dichloromethane; water / 8 h / 20 °C 5.1: Grubb's 2nd generation catalyst / toluene / 1 h / 80 °C / |Inert atmosphere 6.1: tetrakis(triphenylphosphine) palladium(0); silver carbonate / toluene / 4 h / 100 °C / |Inert atmosphere 7.1: methanol; magnesium / benzene / 1 h / 20 °C / |Inert atmosphere 8.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1 h / 20 °C / |Inert atmosphere 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 10.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / |Inert atmosphere 11.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C 12.1: diethyl ether; methanol / 0.25 h / 20 °C / |Inert atmosphere 13.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / |Inert atmosphere 14.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 14.2: 0.5 h / 50 °C / |Inert atmosphere 15.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / |Inert atmosphere View Scheme

1.1: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 80 °C / |Inert atmosphere 2.1: sodium hydrogencarbonate / dichloromethane; water / 8 h / 20 °C 3.1: Grubb's 2nd generation catalyst / toluene / 1 h / 80 °C / |Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); silver carbonate / toluene / 4 h / 100 °C / |Inert atmosphere 5.1: methanol; magnesium / benzene / 1 h / 20 °C / |Inert atmosphere 6.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1 h / 20 °C / |Inert atmosphere 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 8.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / |Inert atmosphere 9.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C 10.1: diethyl ether; methanol / 0.25 h / 20 °C / |Inert atmosphere 11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / |Inert atmosphere 12.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 12.2: 0.5 h / 50 °C / |Inert atmosphere 13.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / |Inert atmosphere View Scheme

1.1: Grubb's 2nd generation catalyst / toluene / 1 h / 80 °C / |Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); silver carbonate / toluene / 4 h / 100 °C / |Inert atmosphere 3.1: methanol; magnesium / benzene / 1 h / 20 °C / |Inert atmosphere 4.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1 h / 20 °C / |Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 6.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / |Inert atmosphere 7.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C 8.1: diethyl ether; methanol / 0.25 h / 20 °C / |Inert atmosphere 9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / |Inert atmosphere 10.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 10.2: 0.5 h / 50 °C / |Inert atmosphere 11.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / |Inert atmosphere View Scheme