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

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

1: tetrahydrofuran / 0.5 h / -40 °C 2: NH4Cl, H2O / tetrahydrofuran / 0.5 h 3: 99 percent / H2 / Pd/C / ethanol / 12 h / 23 °C 4: 87 percent / TFA, H2O / 4 h / 50 °C 5: LiOH, H2O / tetrahydrofuran / 0.5 h / 23 °C 6: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, Et3N / CH2Cl2 / 0.5 h / 23 °C 7: 62 percent / ceric ammonium nitrate, H2O / acetonitrile / 1 h / 23 °C View Scheme

1: 82 percent / Raney Ni / ethanol / 1 h / 0 °C 2: 95 percent / Dess-Martin reagent / CH2Cl2 / 1 h / 23 °C 3: tetrahydrofuran / 0.5 h / -40 °C 4: NH4Cl, H2O / tetrahydrofuran / 0.5 h 5: 99 percent / H2 / Pd/C / ethanol / 12 h / 23 °C 6: 87 percent / TFA, H2O / 4 h / 50 °C 7: LiOH, H2O / tetrahydrofuran / 0.5 h / 23 °C 8: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, Et3N / CH2Cl2 / 0.5 h / 23 °C 9: 62 percent / ceric ammonium nitrate, H2O / acetonitrile / 1 h / 23 °C View Scheme

1: 98 percent / 2,6-lutidine / 12 h / 23 °C 2: 92 percent / NaOMe, MeOH / 5 h / 23 °C 3: 82 percent / Raney Ni / ethanol / 1 h / 0 °C 4: 95 percent / Dess-Martin reagent / CH2Cl2 / 1 h / 23 °C 5: tetrahydrofuran / 0.5 h / -40 °C 6: NH4Cl, H2O / tetrahydrofuran / 0.5 h 7: 99 percent / H2 / Pd/C / ethanol / 12 h / 23 °C 8: 87 percent / TFA, H2O / 4 h / 50 °C 9: LiOH, H2O / tetrahydrofuran / 0.5 h / 23 °C 10: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, Et3N / CH2Cl2 / 0.5 h / 23 °C 11: 62 percent / ceric ammonium nitrate, H2O / acetonitrile / 1 h / 23 °C View Scheme

1: 99 percent / H2 / Pd/C / ethanol / 12 h / 23 °C 2: 87 percent / TFA, H2O / 4 h / 50 °C 3: LiOH, H2O / tetrahydrofuran / 0.5 h / 23 °C 4: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, Et3N / CH2Cl2 / 0.5 h / 23 °C 5: 62 percent / ceric ammonium nitrate, H2O / acetonitrile / 1 h / 23 °C View Scheme

1: 92 percent / NaOMe, MeOH / 5 h / 23 °C 2: 82 percent / Raney Ni / ethanol / 1 h / 0 °C 3: 95 percent / Dess-Martin reagent / CH2Cl2 / 1 h / 23 °C 4: tetrahydrofuran / 0.5 h / -40 °C 5: NH4Cl, H2O / tetrahydrofuran / 0.5 h 6: 99 percent / H2 / Pd/C / ethanol / 12 h / 23 °C 7: 87 percent / TFA, H2O / 4 h / 50 °C 8: LiOH, H2O / tetrahydrofuran / 0.5 h / 23 °C 9: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, Et3N / CH2Cl2 / 0.5 h / 23 °C 10: 62 percent / ceric ammonium nitrate, H2O / acetonitrile / 1 h / 23 °C View Scheme

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

1: 1.) i-Pr2NEt, H2 / 1.) 10percent Pd/C / 1.) EtOH, 23 deg C, 22 h, 2.) MeOH, 50 deg C, 24 h 2: 48percent HF / acetonitrile / 24 h / 23 °C 3: Et3N, oxalyl chloride, DMSO / CH2Cl2 / 2 h / -78 °C 4: 1.) NaClO2, 20percent aq. NaH2PO4, 2.) 1,3-propanedithiol, HCl / 1.) t-BuOH, 2-methyl-2-butene, 23 deg C, 1 h, 2.) CF3CH2OH, 50-55 deg C, 7.5 h 5: 93 percent / Et3N, bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH2Cl2 / 0.5 h / 23 °C View Scheme

1: 1.) O3, 2.) Me2S / 1.) MeOH, CH2Cl2, -78 deg C, 2.) MeOH, a) -78 deg C, 1 h, b) RT, 1 h 2: 91 percent / ammonium formate, AcOH / Pd / 4 h / Heating 3: 90 percent / 0.1 N NaOH / ethanol / 9 h / Ambient temperature 4: 85 percent / Et3N, bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH2Cl2 / 1 h / Ambient temperature View Scheme