tetrabutyl ammonium fluoride in tetrahydrofuran T=70°C; 12 h; Inert atmosphere;

1: With hydrogenchloride in 1,4-dioxane; methanol 0.5 h; Inert atmosphere; 2: With magnesium in 1,4-dioxane; methanol T=20°C; Inert atmosphere; 3: With sodium hydrogencarbonate in 1,4-dioxane; methanol; dichloromethane; water Inert atmosphere; optical yield given as percent ee;

1: With hydrogenchloride in 1,4-dioxane; methanol 0.5 h; Inert atmosphere; 2: With magnesium in 1,4-dioxane; methanol T=20°C; Inert atmosphere; 3: With sodium hydrogencarbonate in 1,4-dioxane; methanol; dichloromethane; water Inert atmosphere; optical yield given as percent ee;

water; potassium carbonate in methanol T=100°C; 12 h;

1: With potassium carbonate; thiophenol in N,N-dimethyl-formamide T=23°C; 2: With tetrabutyl ammonium fluoride in tetrahydrofuran T=70°C;

1: triethylamine / dichloromethane / 0 - 20 °C / |Inert atmosphere 2: palladium diacetate; sodium carbonate; dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine / N,N-dimethyl-formamide; water / 100 °C 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h / 0 - 20 °C 4: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 °C / |Inert atmosphere 5: water; hydrogenchloride / dichloromethane; methanol / 0 - 20 °C 6: triethylamine / dichloromethane / |Inert atmosphere; |Reflux 7: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; ethanol; toluene / 100 °C 8: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h / 0 - 20 °C 9: pyridine / chloroform / |Inert atmosphere; |Reflux 10: trifluoroacetic acid / dichloromethane / 2 h / 0 °C / |Inert atmosphere; |Reflux 11: tris-(dibenzylideneacetone)dipalladium(0); (S)-i-Pr-PHOX / dichloromethane / 20 °C / |Inert atmosphere 12: Grubb's 2nd generation catalyst / 40 °C / |Inert atmosphere 13: triethyl phosphite / 170 °C / |Inert atmosphere 14: water; sodium hydroxide / tetrahydrofuran; methanol / 1 h / |Reflux 15: copper; quinoline / 3 h / 190 °C / |Inert atmosphere 16: sodium; naphthalene / ethylene glycol dimethyl ether / 0.25 h / -78 °C / |Inert atmosphere View Scheme

1.1: palladium on carbon; hydrogen / methanol / 23 °C 2.1: triethylamine / dichloromethane / 0 - 23 °C 3.1: pyridinium tribromide / dichloromethane / 0 - 23 °C 4.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 100 °C 5.1: trichlorophosphate / pyridine / 0 - 23 °C 6.1: 9-BBN / tetrahydrofuran / 23 °C 6.2: 0 - 23 °C 7.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 0 - 23 °C 8.1: potassium carbonate; thiophenol / N,N-dimethyl-formamide / 23 °C 8.2: 70 °C View Scheme

1.1: pyridinium tribromide / dichloromethane / 0 - 23 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 100 °C 3.1: trichlorophosphate / pyridine / 0 - 23 °C 4.1: 9-BBN / tetrahydrofuran / 23 °C 4.2: 0 - 23 °C 5.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 0 - 23 °C 6.1: potassium carbonate; thiophenol / N,N-dimethyl-formamide / 23 °C 6.2: 70 °C View Scheme

1.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 100 °C 2.1: trichlorophosphate / pyridine / 0 - 23 °C 3.1: 9-BBN / tetrahydrofuran / 23 °C 3.2: 0 - 23 °C 4.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 0 - 23 °C 5.1: potassium carbonate; thiophenol / N,N-dimethyl-formamide / 23 °C 5.2: 70 °C View Scheme

1.1: trichlorophosphate / pyridine / 0 - 23 °C 2.1: 9-BBN / tetrahydrofuran / 23 °C 2.2: 0 - 23 °C 3.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 0 - 23 °C 4.1: potassium carbonate; thiophenol / N,N-dimethyl-formamide / 23 °C 4.2: 70 °C View Scheme