1: t-BuOK / dimethylformamide / 15 h / Ambient temperature 2: thionyl chloride / 1.) room temp., 8 h, 2.) 100 deg C, 0.5 h 3: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h View Scheme

1: 1.) t-BuOK / 1.) THF, 0 deg C, 20 min, 2.) THF, RT 2: H2 / 10percent Pd/C / 3040 Torr View Scheme

1.1: NaH / dimethylsulfoxide / 65 °C 1.2: 20 °C 2.1: DCC; DMAP / CH2Cl2 / 2 h / 20 °C 3.1: 39 percent / tetraethylammonium perchlorate / dimethylformamide / 60 °C / Electrochemical reaction View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -10 deg C, 45 min, 2.) THF, hexane, room temperature, overnight 2: 86 percent / H2 / Pd/C / methanol / 6 h 3: H2SO4 / 7 h / Heating View Scheme

1: 78 percent / LDA / tetrahydrofuran / 1 h / Ambient temperature 2: 1) Na, liq. NH3, 2) H3O(1+) 3: 24 percent / PhOPOCl2, DMF / CH2Cl2 / Ambient temperature 4: 89 percent / HCl gas / diethyl ether / 0 °C 5: 55 percent / NaCNBH3 / tetrahydrofuran; H2O / 3 h / Ambient temperature; pH = 4 6: 1) DBU, 2) NaN3 / 1) CH2Cl2, 0 deg C, 2) acetone, H2O, RT 7: 1) H2O, 2) 48percent HBr / 1) 150 deg C, 2 h in autoclave, 2) reflux, 2 h View Scheme

1: t-BuOK / tetrahydrofuran / -78 - 0 °C 2: 430 mg / H2 / Pd/C / ethyl acetate / 24 h / 25 °C View Scheme

potassium tert-butylate in N,N-dimethyl-formamide 15 h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: t-BuOK / dimethylformamide / 15 h / Ambient temperature 2: thionyl chloride / 1.) room temp., 8 h, 2.) 100 deg C, 0.5 h View Scheme

in tetrahydrofuran; water; dimethyl sulfoxide

1: 1.) n-BuLi / 1.) THF, hexane, -10 deg C, 45 min, 2.) THF, hexane, room temperature, overnight 2: 86 percent / H2 / Pd/C / methanol / 6 h 3: H2SO4 / 7 h / Heating 4: LiAlH4 / tetrahydrofuran / 3 h / 0 - 20 °C View Scheme