1.1: NMO; OsO4 / 2-methyl-propan-2-ol; H2O 2.1: H5IO6 3.1: tetrahydrofuran / 0.5 h / -78 °C 4.1: iPr2NEt / CH2Cl2 / -78 °C 5.1: PPTS / ethanol / 20 °C 6.1: 96 percent / NMO; TPAP; mol sieves 4 Angstroem / acetonitrile 7.1: LiHMDS / tetrahydrofuran / -78 °C 7.2: 80 percent / tetrahydrofuran 8.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 8.2: 85 percent / nBu4NF / tetrahydrofuran 9.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 9.2: 60 percent / DMAP / toluene / 80 °C 10.1: 86 percent / TFA / CH2Cl2 / 0 °C 11.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C 12.1: dimethyldioxirane / CH2Cl2 / -50 °C View Scheme

1.1: NMO; OsO4 / 2-methyl-propan-2-ol; H2O 2.1: H5IO6 3.1: tetrahydrofuran / 0.5 h / -78 °C 4.1: iPr2NEt / CH2Cl2 / -78 °C 5.1: PPTS / ethanol / 20 °C 6.1: 96 percent / NMO; TPAP; mol sieves 4 Angstroem / acetonitrile 7.1: LiHMDS / tetrahydrofuran / -78 °C 7.2: 80 percent / tetrahydrofuran 8.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 8.2: 85 percent / nBu4NF / tetrahydrofuran 9.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 9.2: 60 percent / DMAP / toluene / 80 °C 10.1: 86 percent / TFA / CH2Cl2 / 0 °C 11.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme