in acetic acid Ambient temperature;

1: 80 percent / NaH, Bu4NI / dimethylformamide / 3 h / Ambient temperature 2: 87 percent / aq. acetic acid / Ambient temperature View Scheme

1: 1.) p-TsOH, 2.) aq. HOAc / 1.) room temperature, 3 h, 2.) CHCl3 2: KOH / dimethylformamide / 3 h / Ambient temperature 3: aq. HOAc / 0.5 h / 60 °C View Scheme

1: 80 percent / NaH, Bu4NI / dimethylformamide / 3 h / Ambient temperature 2: 87 percent / aq. acetic acid / Ambient temperature View Scheme

1: 76 percent / NaH; tetra-n-butylammonium iodide / tetrahydrofuran / 12 h / 60 °C 2: 60 percent / ZnBr2 / CH2Cl2 / 5 h / 20 °C View Scheme

1: 95 percent / sodium hydride; tetra-n-butylammonium iodide / dimethylformamide / 6 h / 20 °C 2: 72 percent / OsO4; 4-methylmorpholine / acetonitrile; H2O / 12 h / 20 °C View Scheme

1: 76 percent / NaH; tetra-n-butylammonium iodide / tetrahydrofuran / 12 h / 60 °C 2: 60 percent / ZnBr2 / CH2Cl2 / 5 h / 20 °C View Scheme

1.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 20 °C / |Inert atmosphere 2.1: pyridine / 20 °C / |Inert atmosphere 3.1: lipase PS from Burkholderia cepacia / aq. phosphate buffer / 72 h / 30 °C / |Enzymatic reaction 3.2: polymer-supported PPh3 / 1 h / 20 °C 4.1: potassium carbonate / methanol / 0 - 20 °C 5.1: copper(I) bromide / tetrahydrofuran / 1 h / -10 °C / |Inert atmosphere 6.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 7.1: sodium azide / N,N-dimethyl-formamide / 16 h / 20 - 40 °C / |Inert atmosphere 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / |Inert atmosphere 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C / |Inert atmosphere 10.1: palladium 10 on activated carbon; hydrogen / ethanol / 20 °C 11.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 12.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C / |Inert atmosphere 13.1: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 0 - 20 °C / |Inert atmosphere View Scheme

1.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 20 °C / |Inert atmosphere 2.1: pyridine / 20 °C / |Inert atmosphere 3.1: lipase PS from Burkholderia cepacia / aq. phosphate buffer / 72 h / 30 °C / |Enzymatic reaction 3.2: polymer-supported PPh3 / 1 h / 20 °C 4.1: potassium carbonate / methanol / 0 - 20 °C 5.1: copper(I) bromide / tetrahydrofuran / 1 h / -10 °C / |Inert atmosphere 6.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 7.1: sodium azide / N,N-dimethyl-formamide / 16 h / 20 - 40 °C / |Inert atmosphere 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / |Inert atmosphere 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C / |Inert atmosphere 10.1: palladium 10 on activated carbon; hydrogen / ethanol / 20 °C 11.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 12.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C / |Inert atmosphere 13.1: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 0 - 20 °C / |Inert atmosphere View Scheme