1: 10.6 g / LiI / dimethylformamide / 3.5 h / 90 °C 2: 72 percent Turnov. / AgNO2 / diethyl ether / 1.) 0 deg C, 1 d, 2.) r.t., 12 d, in darkness View Scheme

Multi-step reaction with 6 steps 1: 1) t-BuOK / 1) THF, 0 deg C, 30 min, 2) THF, 0 deg C, 4 h2: H2, NaHCO3 / 10percent Pd/C / methanol / 760 Torr3: 14.2 g / KOH / ethanol / Heating4: 83 percent Turnov. / pyridine / CH2Cl2 / 1.) 0 deg C, 2 h, 2.) r.t., 3 h5: DOWEX-50X8-400R, MeOH / 20 h / 50 °C6: Et3N / CH2Cl2 / 1 h / 0 °C  

Multi-step reaction with 7 steps 1: 34 g / toluene / 36 h / Heating2: 1) t-BuOK / 1) THF, 0 deg C, 30 min, 2) THF, 0 deg C, 4 h3: H2, NaHCO3 / 10percent Pd/C / methanol / 760 Torr4: 14.2 g / KOH / ethanol / Heating5: 83 percent Turnov. / pyridine / CH2Cl2 / 1.) 0 deg C, 2 h, 2.) r.t., 3 h6: DOWEX-50X8-400R, MeOH / 20 h / 50 °C7: Et3N / CH2Cl2 / 1 h / 0 °C