1: pyridine, 4-(dimethylamino)pyridine (DMAP) / tetrahydrofuran / 1 h / Ambient temperature 2: 91 percent / EtAlCl2 / CH2Cl2; hexane / 2.5 h / Ambient temperature 3: 96 percent / H2 / 5percent Pt-C / ethyl acetate / 0.83 h / Ambient temperature 4: 30percent KOH / tetrahydrofuran; methanol / 2.5 h / Heating 5: 1) i-Pr2NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h 6: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / Ambient temperature 7: 90 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 5 h / Ambient temperature 8: 1) PhLi / 1) cyclohexane, Et2O, THF, r.t., 30 min, 2) THF, r.t., 30 min 9: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature 10: 1) Hg(OAc)2, 2) NaBH4, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min 11: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature 12: 77 percent / 1,2-dichloro-ethane / 1) reflux, 2 h, 2) r.t., 12 h, 3) reflux, 1 h 13: 82 percent / Bu3SnH / toluene / 1 h / Heating 14: 75 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 5 h / Ambient temperature View Scheme

1: 1) t-BuOK / 1) THF, 55 deg C (bath temp.), 1 h, 2) THF, reflux, 1 h 2: pyridine, 4-(dimethylamino)pyridine (DMAP) / tetrahydrofuran / 1 h / Ambient temperature 3: 91 percent / EtAlCl2 / CH2Cl2; hexane / 2.5 h / Ambient temperature 4: 96 percent / H2 / 5percent Pt-C / ethyl acetate / 0.83 h / Ambient temperature 5: 30percent KOH / tetrahydrofuran; methanol / 2.5 h / Heating 6: 1) i-Pr2NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h 7: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / Ambient temperature 8: 90 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 5 h / Ambient temperature 9: 1) PhLi / 1) cyclohexane, Et2O, THF, r.t., 30 min, 2) THF, r.t., 30 min 10: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature 11: 1) Hg(OAc)2, 2) NaBH4, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min 12: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature 13: 77 percent / 1,2-dichloro-ethane / 1) reflux, 2 h, 2) r.t., 12 h, 3) reflux, 1 h 14: 82 percent / Bu3SnH / toluene / 1 h / Heating 15: 75 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 5 h / Ambient temperature View Scheme

1: 91 percent / EtAlCl2 / CH2Cl2; hexane / 2.5 h / Ambient temperature 2: 96 percent / H2 / 5percent Pt-C / ethyl acetate / 0.83 h / Ambient temperature 3: 30percent KOH / tetrahydrofuran; methanol / 2.5 h / Heating 4: 1) i-Pr2NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h 5: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / Ambient temperature 6: 90 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 5 h / Ambient temperature 7: 1) PhLi / 1) cyclohexane, Et2O, THF, r.t., 30 min, 2) THF, r.t., 30 min 8: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature 9: 1) Hg(OAc)2, 2) NaBH4, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min 10: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature 11: 77 percent / 1,2-dichloro-ethane / 1) reflux, 2 h, 2) r.t., 12 h, 3) reflux, 1 h 12: 82 percent / Bu3SnH / toluene / 1 h / Heating 13: 75 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 5 h / Ambient temperature View Scheme

1: 96 percent / H2 / 5percent Pt-C / ethyl acetate / 0.83 h / Ambient temperature 2: 30percent KOH / tetrahydrofuran; methanol / 2.5 h / Heating 3: 1) i-Pr2NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h 4: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / Ambient temperature 5: 90 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 5 h / Ambient temperature 6: 1) PhLi / 1) cyclohexane, Et2O, THF, r.t., 30 min, 2) THF, r.t., 30 min 7: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature 8: 1) Hg(OAc)2, 2) NaBH4, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min 9: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature 10: 77 percent / 1,2-dichloro-ethane / 1) reflux, 2 h, 2) r.t., 12 h, 3) reflux, 1 h 11: 82 percent / Bu3SnH / toluene / 1 h / Heating 12: 75 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 5 h / Ambient temperature View Scheme

暂无反应条件数据

in methanol; water Yield given. Title compound not separated from byproducts;

1: 1.) sec-butyllithium, hexamethylphosphoramide / 1.) THF, -78 deg C, 2h, 2.) 0 deg C, 1h 2: 71 percent / nickel chloride hexahydrate / 2-methyl-propan-2-ol; H2O / 26 h / 60 °C 3: Raney nickel / ethanol / 4 h / 50 °C 4: p-toluenesulfonic acid monohydrate / ethanol / 1 h / 25 °C View Scheme

1: 71 percent / nickel chloride hexahydrate / 2-methyl-propan-2-ol; H2O / 26 h / 60 °C 2: Raney nickel / ethanol / 4 h / 50 °C 3: p-toluenesulfonic acid monohydrate / ethanol / 1 h / 25 °C View Scheme

1: Raney nickel / ethanol / 4 h / 50 °C 2: p-toluenesulfonic acid monohydrate / ethanol / 1 h / 25 °C View Scheme

1: (i) SOCl2, Py, benzene, (ii) /BRN= 102415/, (iii) /BRN= 1098229/, PhCO2Ag, Et3N, CH2Cl2 2: diethyl ether View Scheme