hydrogen; palladium on activated charcoal in ethanol; ethyl acetate P=760 Torr; 12 h; Ambient temperature;

1: 79 percent / pyridinium dichromate / CH2Cl2 / 22 h / Ambient temperature 2: 1.) tert-butyllithium / 1.) hexane, pentane, 0 deg C, 4.5h 2.) THF, 2h, 0-10 deg C 3: 92 percent / pyridine / 0.5 h / 100 - 110 °C 4: 87 percent / tetraethylammonium fluoride / tetrahydrofuran / 24 h / Ambient temperature 5: 83 percent / H2 / 10percent Pd/C / ethanol; ethyl acetate / 12 h / 760 Torr / Ambient temperature View Scheme

1: 1.) sodium hydride / 1.) DMF, 50 deg C 2.) 50 deg C 2: 79 percent / pyridinium dichromate / CH2Cl2 / 22 h / Ambient temperature 3: 1.) tert-butyllithium / 1.) hexane, pentane, 0 deg C, 4.5h 2.) THF, 2h, 0-10 deg C 4: 92 percent / pyridine / 0.5 h / 100 - 110 °C 5: 87 percent / tetraethylammonium fluoride / tetrahydrofuran / 24 h / Ambient temperature 6: 83 percent / H2 / 10percent Pd/C / ethanol; ethyl acetate / 12 h / 760 Torr / Ambient temperature View Scheme

1: 1.) tert-butyllithium / 1.) hexane, pentane, THF, 2h, 0 degC 2.) room temp., 20h 2: 1.) tert-butyllithium / 1.) hexane, pentane, 0 deg C, 4.5h 2.) THF, 2h, 0-10 deg C 3: 92 percent / pyridine / 0.5 h / 100 - 110 °C 4: 87 percent / tetraethylammonium fluoride / tetrahydrofuran / 24 h / Ambient temperature 5: 83 percent / H2 / 10percent Pd/C / ethanol; ethyl acetate / 12 h / 760 Torr / Ambient temperature View Scheme

1: 1.) tert-butyllithium / 1.) hexane, pentane, 0 deg C, 4.5h 2.) THF, 2h, 0-10 deg C 2: 92 percent / pyridine / 0.5 h / 100 - 110 °C 3: 87 percent / tetraethylammonium fluoride / tetrahydrofuran / 24 h / Ambient temperature 4: 83 percent / H2 / 10percent Pd/C / ethanol; ethyl acetate / 12 h / 760 Torr / Ambient temperature View Scheme

1: 1.) tert-butyllithium / 1.) hexane, pentane, 0 deg C, 4.5h 2.) THF, 2h, 0-10 deg C 2: 92 percent / pyridine / 0.5 h / 100 - 110 °C 3: 87 percent / tetraethylammonium fluoride / tetrahydrofuran / 24 h / Ambient temperature 4: 83 percent / H2 / 10percent Pd/C / ethanol; ethyl acetate / 12 h / 760 Torr / Ambient temperature View Scheme

1: 92 percent / pyridine / 0.5 h / 100 - 110 °C 2: 87 percent / tetraethylammonium fluoride / tetrahydrofuran / 24 h / Ambient temperature 3: 83 percent / H2 / 10percent Pd/C / ethanol; ethyl acetate / 12 h / 760 Torr / Ambient temperature View Scheme

1: 87 percent / tetraethylammonium fluoride / tetrahydrofuran / 24 h / Ambient temperature 2: 83 percent / H2 / 10percent Pd/C / ethanol; ethyl acetate / 12 h / 760 Torr / Ambient temperature View Scheme