1: 74 percent / pyridine 2: N-bromosuccinimide / CCl4 / 0.33 h / Heating 3: tetra-n-butylammonium fluoride / tetra-n-butylammonium bromide / tetrahydrofuran 4: potassium hydroxide / tetrahydrofuran; methanol View Scheme

1: lithium aluminum hydride / tetrahydrofuran / 18 h / 60 °C 2: dichlorodicyanobenzoquinone / dioxane / 15 h / Ambient temperature 3: p-toluenesulfonic acid / CH2Cl2 / 0.5 h / Ambient temperature 4: 72 percent / sodium hydroxide, hydrogen peroxide / methanol; H2O / 1.5 h / Ambient temperature 5: lithium / liquid ammonia; tetrahydrofuran / 1.5 h / -78 °C 6: N,N-diethylcyclohexylamine / dioxane / 1.) 50 deg C, 6 h; 2.) 80 deg C, 2 h 7: aq. HCl; tetrahydrofuran; methanol / Ambient temperature 8: 73 percent / pyridine / 0.5 h / 0 °C 9: 85 percent / dimethylsulfoxide / 4 h / 90 - 100 °C 10: potassium hydroxide / H2O; ethanol / 2 h / Heating 11: methanol; diethyl ether / 1 h / Ambient temperature 12: 81 percent / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 13: 82 percent / aq. HCl; tetrahydrofuran / 72 h / Ambient temperature 14: 74 percent / pyridine 15: N-bromosuccinimide / CCl4 / 0.33 h / Heating 16: tetra-n-butylammonium fluoride / tetra-n-butylammonium bromide / tetrahydrofuran 17: potassium hydroxide / tetrahydrofuran; methanol View Scheme

1: dichlorodicyanobenzoquinone / dioxane / 15 h / Ambient temperature 2: p-toluenesulfonic acid / CH2Cl2 / 0.5 h / Ambient temperature 3: 72 percent / sodium hydroxide, hydrogen peroxide / methanol; H2O / 1.5 h / Ambient temperature 4: lithium / liquid ammonia; tetrahydrofuran / 1.5 h / -78 °C 5: N,N-diethylcyclohexylamine / dioxane / 1.) 50 deg C, 6 h; 2.) 80 deg C, 2 h 6: aq. HCl; tetrahydrofuran; methanol / Ambient temperature 7: 73 percent / pyridine / 0.5 h / 0 °C 8: 85 percent / dimethylsulfoxide / 4 h / 90 - 100 °C 9: potassium hydroxide / H2O; ethanol / 2 h / Heating 10: methanol; diethyl ether / 1 h / Ambient temperature 11: 81 percent / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 12: 82 percent / aq. HCl; tetrahydrofuran / 72 h / Ambient temperature 13: 74 percent / pyridine 14: N-bromosuccinimide / CCl4 / 0.33 h / Heating 15: tetra-n-butylammonium fluoride / tetra-n-butylammonium bromide / tetrahydrofuran 16: potassium hydroxide / tetrahydrofuran; methanol View Scheme

1: 81 percent / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 2: 82 percent / aq. HCl; tetrahydrofuran / 72 h / Ambient temperature 3: 74 percent / pyridine 4: N-bromosuccinimide / CCl4 / 0.33 h / Heating 5: tetra-n-butylammonium fluoride / tetra-n-butylammonium bromide / tetrahydrofuran 6: potassium hydroxide / tetrahydrofuran; methanol View Scheme

1: 73 percent / pyridine / 0.5 h / 0 °C 2: 85 percent / dimethylsulfoxide / 4 h / 90 - 100 °C 3: potassium hydroxide / H2O; ethanol / 2 h / Heating 4: methanol; diethyl ether / 1 h / Ambient temperature 5: 81 percent / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 6: 82 percent / aq. HCl; tetrahydrofuran / 72 h / Ambient temperature 7: 74 percent / pyridine 8: N-bromosuccinimide / CCl4 / 0.33 h / Heating 9: tetra-n-butylammonium fluoride / tetra-n-butylammonium bromide / tetrahydrofuran 10: potassium hydroxide / tetrahydrofuran; methanol View Scheme

1: lithium / liquid ammonia; tetrahydrofuran / 1.5 h / -78 °C 2: N,N-diethylcyclohexylamine / dioxane / 1.) 50 deg C, 6 h; 2.) 80 deg C, 2 h 3: aq. HCl; tetrahydrofuran; methanol / Ambient temperature 4: 73 percent / pyridine / 0.5 h / 0 °C 5: 85 percent / dimethylsulfoxide / 4 h / 90 - 100 °C 6: potassium hydroxide / H2O; ethanol / 2 h / Heating 7: methanol; diethyl ether / 1 h / Ambient temperature 8: 81 percent / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 9: 82 percent / aq. HCl; tetrahydrofuran / 72 h / Ambient temperature 10: 74 percent / pyridine 11: N-bromosuccinimide / CCl4 / 0.33 h / Heating 12: tetra-n-butylammonium fluoride / tetra-n-butylammonium bromide / tetrahydrofuran 13: potassium hydroxide / tetrahydrofuran; methanol View Scheme

1: methanol; diethyl ether / 1 h / Ambient temperature 2: 81 percent / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 3: 82 percent / aq. HCl; tetrahydrofuran / 72 h / Ambient temperature 4: 74 percent / pyridine 5: N-bromosuccinimide / CCl4 / 0.33 h / Heating 6: tetra-n-butylammonium fluoride / tetra-n-butylammonium bromide / tetrahydrofuran 7: potassium hydroxide / tetrahydrofuran; methanol View Scheme

1: 82 percent / aq. HCl; tetrahydrofuran / 72 h / Ambient temperature 2: 74 percent / pyridine 3: N-bromosuccinimide / CCl4 / 0.33 h / Heating 4: tetra-n-butylammonium fluoride / tetra-n-butylammonium bromide / tetrahydrofuran 5: potassium hydroxide / tetrahydrofuran; methanol View Scheme

1: aq. HCl; tetrahydrofuran; methanol / Ambient temperature 2: 73 percent / pyridine / 0.5 h / 0 °C 3: 85 percent / dimethylsulfoxide / 4 h / 90 - 100 °C 4: potassium hydroxide / H2O; ethanol / 2 h / Heating 5: methanol; diethyl ether / 1 h / Ambient temperature 6: 81 percent / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 7: 82 percent / aq. HCl; tetrahydrofuran / 72 h / Ambient temperature 8: 74 percent / pyridine 9: N-bromosuccinimide / CCl4 / 0.33 h / Heating 10: tetra-n-butylammonium fluoride / tetra-n-butylammonium bromide / tetrahydrofuran 11: potassium hydroxide / tetrahydrofuran; methanol View Scheme

1: N-bromosuccinimide / CCl4 / 0.33 h / Heating 2: tetra-n-butylammonium fluoride / tetra-n-butylammonium bromide / tetrahydrofuran 3: potassium hydroxide / tetrahydrofuran; methanol View Scheme