1: NaHCO3; O3 / CH2Cl2; methanol / 1 h / -78 °C 2: 46 percent / PCC; Celite / CH2Cl2 3: 80 percent / p-TsOH*H2O / acetone / 25 h / 20 °C 4: PDC; Celite / dimethylformamide / 52 h / 20 °C 5: 1.11 g / tetrahydrofuran; diethyl ether / 0 °C 6: 97 percent Turnov. / diethyl ether / 20 h / 20 °C 7: 100 percent / p-TsOH*H2O / methanol / 24 h / 60 °C 8: pyridine / 3 h / 20 °C 9: 165 mg / pyridine; 4-(dimethylamino)pyridine / 27 h / 20 °C 10: 99 percent / HF / acetonitrile / 7 h / 20 °C 11: H2CrO4 / acetone / 6 h / 0 - 20 °C 12: aq. NaOH / 10 h / 20 °C 13: 96 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 3 h / 20 °C View Scheme

1: NaHCO3; O3 / CH2Cl2; methanol / 1 h / -78 °C 2: 46 percent / PCC; Celite / CH2Cl2 3: 80 percent / p-TsOH*H2O / acetone / 25 h / 20 °C 4: PDC; Celite / dimethylformamide / 52 h / 20 °C 5: 1.11 g / tetrahydrofuran; diethyl ether / 0 °C 6: 97 percent Turnov. / diethyl ether / 20 h / 20 °C 7: 100 percent / p-TsOH*H2O / methanol / 24 h / 60 °C 8: pyridine / 3 h / 20 °C 9: 165 mg / pyridine; 4-(dimethylamino)pyridine / 27 h / 20 °C 10: 99 percent / HF / acetonitrile / 7 h / 20 °C 11: H2CrO4 / acetone / 6 h / 0 - 20 °C 12: aq. NaOH / 10 h / 20 °C View Scheme