1: 90 percent / DBU / 1.) THF, -0 deg C, 15 min, 2.) THF, H2O, -78 deg C, 0.5 h 2: 95 percent / NaBH(OAc)3 / acetic acid / 1 h / 23 °C 3: 85 percent / pyridine / 10 h / 23 °C 4: 98 percent / 2,6-lutidine / 12 h / 23 °C 5: 92 percent / NaOMe, MeOH / 5 h / 23 °C 6: 82 percent / Raney Ni / ethanol / 1 h / 0 °C 7: 95 percent / Dess-Martin reagent / CH2Cl2 / 1 h / 23 °C 8: tetrahydrofuran / 0.5 h / -40 °C 9: NH4Cl, H2O / tetrahydrofuran / 0.5 h 10: 99 percent / H2 / Pd/C / ethanol / 12 h / 23 °C 11: 87 percent / TFA, H2O / 4 h / 50 °C 12: LiOH, H2O / tetrahydrofuran / 0.5 h / 23 °C 13: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, Et3N / CH2Cl2 / 0.5 h / 23 °C 14: 62 percent / ceric ammonium nitrate, H2O / acetonitrile / 1 h / 23 °C View Scheme