1: 77 percent / NaN3; B(OMe)3 / dimethylformamide / 50 °C 2: 78 percent / PPTS / benzene / Heating 3: 100 percent / H2 / Lindlar catalyst / methanol / 20 °C 4: MnO2; 4 Angstroem molecular sieves / CH2Cl2 / Heating 5: NaCNBH3; AcOH / methanol / 0 °C 6: 83 percent / KHMDS / tetrahydrofuran; toluene / 6 h / -30 °C 7: 93 percent / TPAP; 4-Angstroem molecular sieves; NMO / acetonitrile 8: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0 °C 9: NaBH4 / methanol / 20 °C 10: 96 percent / K2OsO2(OH)4; aq. citric acid; NMO / 2-methyl-propan-2-ol / 20 °C 11: 100 percent / tetrahydrofuran / Heating 12: n-Bu3SnH; AIBN / toluene / Heating 13: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C 14: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 15: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 16: 74 percent / NaOMe / methanol / 20 °C 17: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme

1: 77 percent / NaN3; B(OMe)3 / dimethylformamide / 50 °C 2: 78 percent / PPTS / benzene / Heating 3: 100 percent / H2 / Lindlar catalyst / methanol / 20 °C 4: MnO2; 4 Angstroem molecular sieves / CH2Cl2 / Heating 5: NaCNBH3; AcOH / methanol / 0 °C 6: 83 percent / KHMDS / tetrahydrofuran; toluene / 6 h / -30 °C 7: 93 percent / TPAP; 4-Angstroem molecular sieves; NMO / acetonitrile 8: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0 °C 9: NaBH4 / methanol / 20 °C 10: 96 percent / K2OsO2(OH)4; aq. citric acid; NMO / 2-methyl-propan-2-ol / 20 °C 11: 100 percent / tetrahydrofuran / Heating 12: n-Bu3SnH; AIBN / toluene / Heating 13: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C 14: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 15: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 16: 74 percent / NaOMe / methanol / 20 °C View Scheme