MMPP in methanol; water T=15 - 20°C; Dakin reaction; 24 h;

1: 85 percent / tetrahydrofuran / 5 - 20 °C 2: DDQ / dioxane / 1 h View Scheme

1: 90 percent / Cl2 2: 66 percent / K2CO3 / dimethylformamide / 0.08 h / Heating 3: 100 percent / NaBH4 / aq. ethanol / 1 h / 25 °C 4: 97 percent / 12N aq. HCl 5: 96 percent / dimethylsulfoxide / 1.25 h 6: 74 percent / borane / tetrahydrofuran / 1.5 h / Heating View Scheme

1: 95 percent / anhydrous potassium carbonate / dimethylformamide / 2 h / 100 °C 2: 96 percent / sodium borohydride / ethanol / 1 h / Ambient temperature 3: 95 percent / pyridine / 0.5 h / Ambient temperature; addition of reagent at ice-bath cooling 4: 94 percent / sodium acetate, bromine / acetic acid / 1 h / Ambient temperature; addition of bromine at 15 deg C 5: 94 percent / potassium hydroxide / methanol / 0.5 h / Ambient temperature 6: 79 percent / potassium permanganate / acetone; H2O / Heating 7: oxalyl chloride, pyridine / benzene / 1 h / ice-bath cooling 8: 65 percent / triethylamine / benzene / ice-bath cooling 9: 96 percent / 10percent hydrochlorid acid / ethanol / 0.5 h / Heating 10: 15 percent / potassium ferricyanide, 5percent sodium hydrogen carbonate / CHCl3; H2O / 1.5 h / 60 °C 11: 50 percent / fermentation by Nematopora corylii CBS2608 12: 96 percent / lithium aluminium hydride / dioxane / 2 h / Heating; addition of the reagent at room temperature within 30 min View Scheme

1.1: K2CO3 / ethanol / 2 h / 75 °C 2.1: 100 percent / sodium acetate / 0.08 h / microwave irradiation 3.1: NaOH / 90 °C 3.2: 81 percent / H2O2 View Scheme

1: 90 percent / Cl2 2: 66 percent / K2CO3 / dimethylformamide / 0.08 h / Heating 3: 100 percent / NaBH4 / aq. ethanol / 1 h / 25 °C 4: 97 percent / 12N aq. HCl 5: 96 percent / dimethylsulfoxide / 1.25 h 6: 74 percent / borane / tetrahydrofuran / 1.5 h / Heating 7: 19 percent / 2.5 h / Heating 8: 69 percent / TFA, 36 N H2SO4 / 3.5 h / 25 °C View Scheme

1.1: 90 percent / K2CO3 2.1: 91 percent / NH4OAc 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: ZnCl2 / tetrahydrofuran / 0.75 h / -78 - 0 °C 3.3: 80 percent / tetrahydrofuran / -78 - 20 °C 4.1: 72 percent / aq. H2SO4 5.1: 80 percent / NaBH4; NiCl2 / ethanol View Scheme

1.1: 92 percent / triethylamine / dimethylformamide / 20 °C 2.1: n-BuLi / tetrahydrofuran / 3 h / -78 °C 2.2: tetrahydrofuran / 5 h / 20 °C 3.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme

1: acetic anhydride; triethylamine / 6 h / 110 °C 2: quinoline; copper / 3 h / 200 °C / Inert atmosphere View Scheme

1: 391.5 g / potassium carbonate / dimethylformamide / 3 h / 100 °C 2: 391 g / hydroxylamine hydrochloride; pyridine / methanol / 1 h / Heating 3: 349 g / acetic anhydride / 3 h / 110 °C 4: 329 g / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C View Scheme