in water T=20°C; 0.25 h; 105000 g particle fraction of potato homogenate;

1: 88 percent / CHCl3; pyridine / 1.)0 deg C, 1 h, 2.)22 deg C, 14 h 2: 96 percent / K2CO3, H2O / methanol / 1 h / Heating 3: oxalyl chloride / CH2Cl2; dimethylformamide / 0.75 h / 0 °C 4: 22 percent / 1M sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C 5: 99 percent / H2 / Lindlar's catalyst / benzene / 0.33 h / 760 Torr 6: 53 percent / lithium diisopropylaminde / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -108 °C 7: 70 percent Turnov. / 1M triethylaluminum, tetrakis(triphenylphosphine)palladium(0) / hexane; 1,2-dichloro-ethane / 10.5 h / 20 °C 8: 96 percent / KOH / H2O; methanol / 4 h / Heating 9: triethylamine / CH2Cl2 / 0.5 h / -23 °C 10: 100 percent / NaCN / dimethylsulfoxide / 5 h / 20 °C 11: KOH / ethanol / 5 h / Heating View Scheme

1: 98 percent / NaBH4 / ethanol / 0.33 h / 0 °C 2: 88 percent / CHCl3; pyridine / 1.)0 deg C, 1 h, 2.)22 deg C, 14 h 3: 96 percent / K2CO3, H2O / methanol / 1 h / Heating 4: oxalyl chloride / CH2Cl2; dimethylformamide / 0.75 h / 0 °C 5: 22 percent / 1M sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C 6: 99 percent / H2 / Lindlar's catalyst / benzene / 0.33 h / 760 Torr 7: 53 percent / lithium diisopropylaminde / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -108 °C 8: 70 percent Turnov. / 1M triethylaluminum, tetrakis(triphenylphosphine)palladium(0) / hexane; 1,2-dichloro-ethane / 10.5 h / 20 °C 9: 96 percent / KOH / H2O; methanol / 4 h / Heating 10: triethylamine / CH2Cl2 / 0.5 h / -23 °C 11: 100 percent / NaCN / dimethylsulfoxide / 5 h / 20 °C 12: KOH / ethanol / 5 h / Heating View Scheme

1: 22 percent / 1M sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C 2: 99 percent / H2 / Lindlar's catalyst / benzene / 0.33 h / 760 Torr 3: 53 percent / lithium diisopropylaminde / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -108 °C 4: 70 percent Turnov. / 1M triethylaluminum, tetrakis(triphenylphosphine)palladium(0) / hexane; 1,2-dichloro-ethane / 10.5 h / 20 °C 5: 96 percent / KOH / H2O; methanol / 4 h / Heating 6: triethylamine / CH2Cl2 / 0.5 h / -23 °C 7: 100 percent / NaCN / dimethylsulfoxide / 5 h / 20 °C 8: KOH / ethanol / 5 h / Heating View Scheme

1: oxalyl chloride / CH2Cl2; dimethylformamide / 0.75 h / 0 °C 2: 22 percent / 1M sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C 3: 99 percent / H2 / Lindlar's catalyst / benzene / 0.33 h / 760 Torr 4: 53 percent / lithium diisopropylaminde / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -108 °C 5: 70 percent Turnov. / 1M triethylaluminum, tetrakis(triphenylphosphine)palladium(0) / hexane; 1,2-dichloro-ethane / 10.5 h / 20 °C 6: 96 percent / KOH / H2O; methanol / 4 h / Heating 7: triethylamine / CH2Cl2 / 0.5 h / -23 °C 8: 100 percent / NaCN / dimethylsulfoxide / 5 h / 20 °C 9: KOH / ethanol / 5 h / Heating View Scheme

1: 96 percent / K2CO3, H2O / methanol / 1 h / Heating 2: oxalyl chloride / CH2Cl2; dimethylformamide / 0.75 h / 0 °C 3: 22 percent / 1M sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C 4: 99 percent / H2 / Lindlar's catalyst / benzene / 0.33 h / 760 Torr 5: 53 percent / lithium diisopropylaminde / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -108 °C 6: 70 percent Turnov. / 1M triethylaluminum, tetrakis(triphenylphosphine)palladium(0) / hexane; 1,2-dichloro-ethane / 10.5 h / 20 °C 7: 96 percent / KOH / H2O; methanol / 4 h / Heating 8: triethylamine / CH2Cl2 / 0.5 h / -23 °C 9: 100 percent / NaCN / dimethylsulfoxide / 5 h / 20 °C 10: KOH / ethanol / 5 h / Heating View Scheme

1: 99 percent / H2 / Lindlar's catalyst / benzene / 0.33 h / 760 Torr 2: 53 percent / lithium diisopropylaminde / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -108 °C 3: 70 percent Turnov. / 1M triethylaluminum, tetrakis(triphenylphosphine)palladium(0) / hexane; 1,2-dichloro-ethane / 10.5 h / 20 °C 4: 96 percent / KOH / H2O; methanol / 4 h / Heating 5: triethylamine / CH2Cl2 / 0.5 h / -23 °C 6: 100 percent / NaCN / dimethylsulfoxide / 5 h / 20 °C 7: KOH / ethanol / 5 h / Heating View Scheme

lithium hydroxide in ethylene glycol dimethyl ether; water T=23°C; 3 h;

potassium hydroxide in ethanol 5 h; Heating;

1: 1.) supernatant from potato homogenate / pH=7 2: LiOH / 1,2-dimethoxy-ethane; H2O / 3 h / 23 °C View Scheme