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

sodium hydrogencarbonate; sodium iodide in acetone 3 h; Heating; Yield given;

sodium hydrogencarbonate; lithium bromide in acetone

Multi-step reaction with 3 steps 1: 90 percent / imidazole / dimethylformamide / 16 h / Ambient temperature2: 72 percent / Na, NH3 (liquid) / tetrahydrofuran / 1.5 h / -35 °C3: pyridine / 14 h / 0 °C