1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min 2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature 3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 4: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 5: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 6: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 7: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating 8: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating View Scheme

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min 2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature View Scheme

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min 2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature 3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 4: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 5: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 6: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 7: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating 8: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating 9: 55 percent / aq. NaOH / Ambient temperature View Scheme

aluminum oxide; trimethylsilyl trifluoromethanesulfonate in methanol

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min 2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature 3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 4: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 5: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 6: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 7: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating 8: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating 9: 55 percent / aq. NaOH / Ambient temperature 10: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature View Scheme

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min 2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature 3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 4: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 5: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 6: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h View Scheme

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min 2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature 3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 4: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 5: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 6: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 7: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating View Scheme

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min 2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature 3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 4: 1.) red mercuric oxide, mercuric chloride, 2.) sodium borohydride / 1.) aq. THF, RT 90 min, 2.) ethanol, water, RT, 30 min 5: 77 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h 6: 66 percent / nitric acid, iodine / dioxane / 3 h / Heating View Scheme

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min 2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature 3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 4: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 5: 58 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h View Scheme

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min 2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature 3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 4: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 5: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 6: 81 percent / pyridine / 3.5 h / 103 °C 7: 98.5 percent / 4-dimethylaminopyridine (DMAP) / acetonitrile / Ambient temperature 8: 27 percent / α,α-azobis(isobutyronitrile) (AIBN), tributyltin hydride / toluene / 3 h / 75 - 80 °C 9: 61 percent / dichloroacetic acid / CH2Cl2 / 0.5 h / Ambient temperature 10: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran 11: 46 percent / iodine, nitric acid / dioxane / 3 h / Heating View Scheme