oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-55 - -40°C; 0.5 h;

triethylamine in ethanol T=40 - 80°C; 72 h; Product distribution / selectivity;

1: With acetic acid in ethanol; water Heating / reflux; 2: With triethylamine in ethanol; water T=0 - 80°C; 22 h;

1: 89.5 percent 2: 95 percent / 1.) LiAlH4, air; 2.) HCl 3: 80 percent / NEt3 / (-)-narwedine / ethanol View Scheme

1: 95 percent / 1.) LiAlH4, air; 2.) HCl 2: 80 percent / NEt3 / (-)-narwedine / ethanol View Scheme

1.1: potassium hexacyanoferrate(III); potassium carbonate / toluene / 1 h / 50 - 60 °C / |Large scale 2.1: toluene-4-sulfonic acid / toluene / |Reflux; |Large scale 3.1: lithium aluminium tetrahydride; hydrogen / tetrahydrofuran / 3 h / 60 - 65 °C / |Inert atmosphere; |Large scale 3.2: 0.25 h / |Large scale 3.3: 0.33 h / 60 °C / pH < 1 / |Large scale 4.1: triethylamine / ethanol / |Reflux; |Large scale View Scheme

1.1: sulfuric acid / 6 h / 90 °C / |Inert atmosphere; |Large scale 2.1: ethanol / 4 h / |Reflux; |Large scale 3.1: sodium hydroxide; sodium tetrahydroborate / water / 1 h / 20 °C / |Large scale 4.1: formic acid / 1,4-dioxane; N,N-dimethyl-formamide / 10 h / |Reflux; |Large scale 5.1: potassium hexacyanoferrate(III); potassium carbonate / toluene / 1 h / 50 - 60 °C / |Large scale 6.1: toluene-4-sulfonic acid / toluene / |Reflux; |Large scale 7.1: lithium aluminium tetrahydride; hydrogen / tetrahydrofuran / 3 h / 60 - 65 °C / |Inert atmosphere; |Large scale 7.2: 0.25 h / |Large scale 7.3: 0.33 h / 60 °C / pH < 1 / |Large scale 8.1: triethylamine / ethanol / |Reflux; |Large scale View Scheme

1.1: bromine / methanol / 5 - 40 °C / |Large scale 2.1: sulfuric acid / 6 h / 90 °C / |Inert atmosphere; |Large scale 3.1: ethanol / 4 h / |Reflux; |Large scale 4.1: sodium hydroxide; sodium tetrahydroborate / water / 1 h / 20 °C / |Large scale 5.1: formic acid / 1,4-dioxane; N,N-dimethyl-formamide / 10 h / |Reflux; |Large scale 6.1: potassium hexacyanoferrate(III); potassium carbonate / toluene / 1 h / 50 - 60 °C / |Large scale 7.1: toluene-4-sulfonic acid / toluene / |Reflux; |Large scale 8.1: lithium aluminium tetrahydride; hydrogen / tetrahydrofuran / 3 h / 60 - 65 °C / |Inert atmosphere; |Large scale 8.2: 0.25 h / |Large scale 8.3: 0.33 h / 60 °C / pH < 1 / |Large scale 9.1: triethylamine / ethanol / |Reflux; |Large scale View Scheme

1.1: ethanol / 4 h / |Reflux; |Large scale 2.1: sodium hydroxide; sodium tetrahydroborate / water / 1 h / 20 °C / |Large scale 3.1: formic acid / 1,4-dioxane; N,N-dimethyl-formamide / 10 h / |Reflux; |Large scale 4.1: potassium hexacyanoferrate(III); potassium carbonate / toluene / 1 h / 50 - 60 °C / |Large scale 5.1: toluene-4-sulfonic acid / toluene / |Reflux; |Large scale 6.1: lithium aluminium tetrahydride; hydrogen / tetrahydrofuran / 3 h / 60 - 65 °C / |Inert atmosphere; |Large scale 6.2: 0.25 h / |Large scale 6.3: 0.33 h / 60 °C / pH < 1 / |Large scale 7.1: triethylamine / ethanol / |Reflux; |Large scale View Scheme

1.1: formic acid / 1,4-dioxane; N,N-dimethyl-formamide / 10 h / |Reflux; |Large scale 2.1: potassium hexacyanoferrate(III); potassium carbonate / toluene / 1 h / 50 - 60 °C / |Large scale 3.1: toluene-4-sulfonic acid / toluene / |Reflux; |Large scale 4.1: lithium aluminium tetrahydride; hydrogen / tetrahydrofuran / 3 h / 60 - 65 °C / |Inert atmosphere; |Large scale 4.2: 0.25 h / |Large scale 4.3: 0.33 h / 60 °C / pH < 1 / |Large scale 5.1: triethylamine / ethanol / |Reflux; |Large scale View Scheme