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 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

palladium on activated charcoal; acetic acid Hydrogenation;