1: 1) NaH / 1) DMF, 0 deg C, 40 min, 2) r.t., 30 min 2: 81 percent / pTsOH*H2O / methanol / 7 h / 0 °C 3: 1) pyridine, 2) pyridine / 1) 0 deg C, 27 h, 2) r.t., 6 h 4: 84 percent / NaOMe / methanol / 3 h / Ambient temperature 5: 91 percent / LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 6: 1) NaH / 1) DMF, 0 deg C, 45 min, 2) r.t., 12 h 7: 92 percent / pTsOH / methanol / 4 h / Ambient temperature 8: 87 percent / pyridine / 13 h / 70 °C 9: 98 percent / pTsOH / CH2Cl2 / 0.5 h / Ambient temperature 10: 89 percent / NaOMe / methanol / 9 h / 50 °C 11: 87 percent / PCC, molecular sieves / CH2Cl2 / 6 h / Ambient temperature 12: 43 percent / KOtBu / toluene / 6 h / Ambient temperature 13: 97 percent / pyridinium toluene-p-sulfonate / ethanol / 4 h / 50 °C 14: 100 percent / pyridine / 2 h / Ambient temperature 15: 72 percent / DDQ, H2O / CH2Cl2 / 18 h / Ambient temperature 16: 27 percent / molecular sieves, BF3*OEt2 / 1,2-dichloro-ethane / 0.33 h / 0 °C 17: 100 percent / NaOMe, MeOH / 2 h / 0 °C View Scheme