1: imidazole / dimethylformamide / 18 h / Ambient temperature 2: 91 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 3: pyridine / CH2Cl2 / 15 h / 4 °C 4: NaI, NaHCO3 / acetone / 3 h / Heating 5: 1.) 1.66M BuLi / 1.) hexane, HMPA, THF, 0 deg C - 5 deg C, 40 min, 2.) hexane, HMPA, THF, r.t., 1 h 6: H2, quinoline / 5percent Pd/BaSO4 / methanol / 760 Torr 7: pyridine / CH2Cl2 / 14 h / 4 °C 8: LiBr, NaHCO3 / acetone / 24 h / Ambient temperature 9: 67 percent / KOH / methanol; aq. ethanol / 3 h / 65 °C 10: 91 percent / 1.0M tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 11: 97 percent / H2 / platinum oxide / hexane; diethyl ether; acetic acid / 96 h / 760 Torr View Scheme

1: NaBH4 / tetrahydrofuran; H2O / 0.67 h / -6 - -2 °C 2: imidazole / dimethylformamide / 18 h / Ambient temperature 3: 91 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 4: pyridine / CH2Cl2 / 15 h / 4 °C 5: NaI, NaHCO3 / acetone / 3 h / Heating 6: 1.) 1.66M BuLi / 1.) hexane, HMPA, THF, 0 deg C - 5 deg C, 40 min, 2.) hexane, HMPA, THF, r.t., 1 h 7: H2, quinoline / 5percent Pd/BaSO4 / methanol / 760 Torr 8: pyridine / CH2Cl2 / 14 h / 4 °C 9: LiBr, NaHCO3 / acetone / 24 h / Ambient temperature 10: 67 percent / KOH / methanol; aq. ethanol / 3 h / 65 °C 11: 91 percent / 1.0M tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 12: 97 percent / H2 / platinum oxide / hexane; diethyl ether; acetic acid / 96 h / 760 Torr View Scheme

1: 1.) 1.66M BuLi / 1.) hexane, HMPA, THF, 0 deg C - 5 deg C, 40 min, 2.) hexane, HMPA, THF, r.t., 1 h 2: H2, quinoline / 5percent Pd/BaSO4 / methanol / 760 Torr 3: pyridine / CH2Cl2 / 14 h / 4 °C 4: LiBr, NaHCO3 / acetone / 24 h / Ambient temperature 5: 67 percent / KOH / methanol; aq. ethanol / 3 h / 65 °C 6: 91 percent / 1.0M tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 7: 97 percent / H2 / platinum oxide / hexane; diethyl ether; acetic acid / 96 h / 760 Torr View Scheme

1: pyridine / CH2Cl2 / 15 h / 4 °C 2: NaI, NaHCO3 / acetone / 3 h / Heating 3: 1.) 1.66M BuLi / 1.) hexane, HMPA, THF, 0 deg C - 5 deg C, 40 min, 2.) hexane, HMPA, THF, r.t., 1 h 4: H2, quinoline / 5percent Pd/BaSO4 / methanol / 760 Torr 5: pyridine / CH2Cl2 / 14 h / 4 °C 6: LiBr, NaHCO3 / acetone / 24 h / Ambient temperature 7: 67 percent / KOH / methanol; aq. ethanol / 3 h / 65 °C 8: 91 percent / 1.0M tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 9: 97 percent / H2 / platinum oxide / hexane; diethyl ether; acetic acid / 96 h / 760 Torr View Scheme

1: NaI, NaHCO3 / acetone / 3 h / Heating 2: 1.) 1.66M BuLi / 1.) hexane, HMPA, THF, 0 deg C - 5 deg C, 40 min, 2.) hexane, HMPA, THF, r.t., 1 h 3: H2, quinoline / 5percent Pd/BaSO4 / methanol / 760 Torr 4: pyridine / CH2Cl2 / 14 h / 4 °C 5: LiBr, NaHCO3 / acetone / 24 h / Ambient temperature 6: 67 percent / KOH / methanol; aq. ethanol / 3 h / 65 °C 7: 91 percent / 1.0M tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 8: 97 percent / H2 / platinum oxide / hexane; diethyl ether; acetic acid / 96 h / 760 Torr View Scheme

1: H2, quinoline / 5percent Pd/BaSO4 / methanol / 760 Torr 2: pyridine / CH2Cl2 / 14 h / 4 °C 3: LiBr, NaHCO3 / acetone / 24 h / Ambient temperature 4: 67 percent / KOH / methanol; aq. ethanol / 3 h / 65 °C 5: 91 percent / 1.0M tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 6: 97 percent / H2 / platinum oxide / hexane; diethyl ether; acetic acid / 96 h / 760 Torr View Scheme

1: 91 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 2: pyridine / CH2Cl2 / 15 h / 4 °C 3: NaI, NaHCO3 / acetone / 3 h / Heating 4: 1.) 1.66M BuLi / 1.) hexane, HMPA, THF, 0 deg C - 5 deg C, 40 min, 2.) hexane, HMPA, THF, r.t., 1 h 5: H2, quinoline / 5percent Pd/BaSO4 / methanol / 760 Torr 6: pyridine / CH2Cl2 / 14 h / 4 °C 7: LiBr, NaHCO3 / acetone / 24 h / Ambient temperature 8: 67 percent / KOH / methanol; aq. ethanol / 3 h / 65 °C 9: 91 percent / 1.0M tetrabutylammonium fluoride / tetrahydrofuran / 5 h / Ambient temperature 10: 97 percent / H2 / platinum oxide / hexane; diethyl ether; acetic acid / 96 h / 760 Torr View Scheme

copper(I) bromide in tetrahydrofuran T=-40 - 20°C; 40 h; Yield given. Yields of byproduct given;

1: With [RuH(CO)(dppp)(ampy)]Cl T=90°C; 0.0833333 h; Inert atmosphereSchlenk technique; 2: With sodium isopropanolate in isopropyl alcohol 0.166667 h; Inert atmosphereSchlenk technique;

perchloric acid; mercury(II) oxide in ethylene glycol dimethyl ether