1: 93 percent / TPAP; 4-Angstroem molecular sieves; NMO / acetonitrile 2: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0 °C 3: NaBH4 / methanol / 20 °C 4: 96 percent / K2OsO2(OH)4; aq. citric acid; NMO / 2-methyl-propan-2-ol / 20 °C 5: 100 percent / tetrahydrofuran / Heating 6: n-Bu3SnH; AIBN / toluene / Heating 7: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C 8: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 9: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 10: 74 percent / NaOMe / methanol / 20 °C 11: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme

1: 93 percent / TPAP; 4-Angstroem molecular sieves; NMO / acetonitrile 2: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0 °C 3: NaBH4 / methanol / 20 °C 4: 96 percent / K2OsO2(OH)4; aq. citric acid; NMO / 2-methyl-propan-2-ol / 20 °C 5: 100 percent / tetrahydrofuran / Heating 6: n-Bu3SnH; AIBN / toluene / Heating 7: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C 8: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 9: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 10: 74 percent / NaOMe / methanol / 20 °C View Scheme