1: 100 percent / N-bromosuccinimide, DMSO / tetrahydrofuran / 6 h / 0 °C 2: 79 percent / azobis(isobutyronitrile), tri-n-butyltin hydride / toluene / 4 h / 120 °C 3: 87 percent / pyridinium dichromate, 3A molecular sieves / CH2Cl2 / 4 h / Ambient temperature 4: 1.) 5 N sodium hydroxide, 2.) p-toluenesulfonic acid / 1.) THF, H2O, 26 h, r. t., 2.) aq. EtOH, 60 - 65 deg C, 24 h 5: 74 percent / xylene / 36 h / 210 °C 6: 94 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / Ambient temperature 7: 93 percent / 2,6-lutidine / CH2Cl2 / 4 h / 0 °C 8: 1.) lithium hexamethyldisilazide, 2.) acetic acid / 1.) THF, 0 deg C, 40 min, 2.) THF, -78 deg C, 10 min 9: 79 percent / triethylammonium fluoride / acetonitrile / 72 h / Ambient temperature View Scheme

1: 1.) 5 N sodium hydroxide, 2.) p-toluenesulfonic acid / 1.) THF, H2O, 26 h, r. t., 2.) aq. EtOH, 60 - 65 deg C, 24 h 2: 74 percent / xylene / 36 h / 210 °C 3: 94 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / Ambient temperature 4: 93 percent / 2,6-lutidine / CH2Cl2 / 4 h / 0 °C 5: 1.) lithium hexamethyldisilazide, 2.) acetic acid / 1.) THF, 0 deg C, 40 min, 2.) THF, -78 deg C, 10 min 6: 79 percent / triethylammonium fluoride / acetonitrile / 72 h / Ambient temperature View Scheme

1: 96 percent / 5 N aq. sodium hydroxide / methanol; H2O / 8 h / 60 °C 2: 2.) 4-(dimethylamino)pyridine, trimethylamine / 1.) ether, THF, 10 min, 2.) CH2Cl2, 0 deg C, 30 min, 3.) CH2Cl2, 10 min, r. t. 3: 100 percent / N-bromosuccinimide, DMSO / tetrahydrofuran / 6 h / 0 °C 4: 79 percent / azobis(isobutyronitrile), tri-n-butyltin hydride / toluene / 4 h / 120 °C 5: 87 percent / pyridinium dichromate, 3A molecular sieves / CH2Cl2 / 4 h / Ambient temperature 6: 1.) 5 N sodium hydroxide, 2.) p-toluenesulfonic acid / 1.) THF, H2O, 26 h, r. t., 2.) aq. EtOH, 60 - 65 deg C, 24 h 7: 74 percent / xylene / 36 h / 210 °C 8: 94 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / Ambient temperature 9: 93 percent / 2,6-lutidine / CH2Cl2 / 4 h / 0 °C 10: 1.) lithium hexamethyldisilazide, 2.) acetic acid / 1.) THF, 0 deg C, 40 min, 2.) THF, -78 deg C, 10 min 11: 79 percent / triethylammonium fluoride / acetonitrile / 72 h / Ambient temperature View Scheme

1: 2.) 4-(dimethylamino)pyridine, trimethylamine / 1.) ether, THF, 10 min, 2.) CH2Cl2, 0 deg C, 30 min, 3.) CH2Cl2, 10 min, r. t. 2: 100 percent / N-bromosuccinimide, DMSO / tetrahydrofuran / 6 h / 0 °C 3: 79 percent / azobis(isobutyronitrile), tri-n-butyltin hydride / toluene / 4 h / 120 °C 4: 87 percent / pyridinium dichromate, 3A molecular sieves / CH2Cl2 / 4 h / Ambient temperature 5: 1.) 5 N sodium hydroxide, 2.) p-toluenesulfonic acid / 1.) THF, H2O, 26 h, r. t., 2.) aq. EtOH, 60 - 65 deg C, 24 h 6: 74 percent / xylene / 36 h / 210 °C 7: 94 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / Ambient temperature 8: 93 percent / 2,6-lutidine / CH2Cl2 / 4 h / 0 °C 9: 1.) lithium hexamethyldisilazide, 2.) acetic acid / 1.) THF, 0 deg C, 40 min, 2.) THF, -78 deg C, 10 min 10: 79 percent / triethylammonium fluoride / acetonitrile / 72 h / Ambient temperature View Scheme

1: 93 percent / 2,6-lutidine / CH2Cl2 / 4 h / 0 °C 2: 1.) lithium hexamethyldisilazide, 2.) acetic acid / 1.) THF, 0 deg C, 40 min, 2.) THF, -78 deg C, 10 min 3: 79 percent / triethylammonium fluoride / acetonitrile / 72 h / Ambient temperature View Scheme

1.1: 99 percent / H2 / 10percent Pd/C / ethyl acetate / 6 h / 2482.38 Torr 2.1: 82 percent / LiAlH4 / diethyl ether / 24 h / Heating 3.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 4.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 5.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 6.1: 100 percent / K2CO3 / methanol / 1.5 h / 20 °C 7.1: 100 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - -40 °C 8.1: 90 percent / NaOMe / methanol / 20 °C 9.1: 93 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C 10.1: 95 percent / 2-methyl-2-butene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 20 °C 11.1: CDI / tetrahydrofuran / 3 h / 20 °C 11.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 12.1: CDI / tetrahydrofuran / 3 h / 20 °C 12.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 13.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 14.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 14.2: 62 percent / benzene; CHCl3 / Heating 15.1: 47 percent / LDA; Py*HCl / tetrahydrofuran / -78 - 20 °C 16.1: 81 percent / MgBr2*Et2O; EtSH / diethyl ether; benzene / 11 h / 0 - 20 °C View Scheme

1: 87 percent / AcOH / 13 h / 49 °C 2: 71 percent / H2 / 10percent Pd/C / ethyl acetate / 40 h / 22 °C 3: 80.5 percent / acetic acid; tetrahydrofuran / 3 h / 20 °C 4: 32.1 percent / aq. HCl / dioxane / 51 h / 41 - 43 °C 5: 85 percent / methanol; diethyl ether / 0 - 5 °C 6: 84 percent / LiEt3BH / tetrahydrofuran / 1 h / -78 °C 7: ZnCl2, 4 Angstroem molecular sieves / tetrahydrofuran / 2.5 h / Heating View Scheme

1: 71 percent / H2 / 10percent Pd/C / ethyl acetate / 40 h / 22 °C 2: 80.5 percent / acetic acid; tetrahydrofuran / 3 h / 20 °C 3: 32.1 percent / aq. HCl / dioxane / 51 h / 41 - 43 °C 4: 85 percent / methanol; diethyl ether / 0 - 5 °C 5: 84 percent / LiEt3BH / tetrahydrofuran / 1 h / -78 °C 6: ZnCl2, 4 Angstroem molecular sieves / tetrahydrofuran / 2.5 h / Heating View Scheme

titanium tetrachloride; zinc in tetrahydrofuran T=-20 - -10°C; McMurry reaction; 4 h; Inert atmosphere;

titanium tetrachloride; zinc in tetrahydrofuran T=-20 - -10°C; McMurry reaction; 4 h; Inert atmosphere;