1.1: 75 percent / Et3N; DMAP / CH2Cl2 / 0 - 20 °C 2.1: aq. AcOH / tetrahydrofuran / 3.5 h / 30 °C 3.1: 101 mg / TPAP; NMO; molecular sieves / CH2Cl2 / 0.33 h 4.1: LDA / tetrahydrofuran / 0.58 h / -78 - -40 °C 4.2: 86 percent / tetrahydrofuran / 1 h / -78 °C 5.1: 91 percent / pyridine / CH2Cl2 / 2 h 6.1: 86 percent / OsO4; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 18 h / 20 °C 7.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0 °C 8.1: HF*pyridine / tetrahydrofuran / 1.5 h / 20 °C 9.1: 63.2 mg / NaClO2; 2-methyl-2-butene; aq. citric acid/Na2HPO4 / 2-methyl-propan-2-ol / 1.5 h / 0 °C / pH 3.6 10.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 0.5 h / 0 °C 10.2: 74 percent / DMAP / tetrahydrofuran; toluene / 3 h 11.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 12.1: 38 percent / HF*pyridine / 168 h / 35 - 40 °C View Scheme

1.1: LDA / tetrahydrofuran / 0.58 h / -78 - -40 °C 1.2: 86 percent / tetrahydrofuran / 1 h / -78 °C 2.1: 91 percent / pyridine / CH2Cl2 / 2 h 3.1: 86 percent / OsO4; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 18 h / 20 °C 4.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0 °C 5.1: HF*pyridine / tetrahydrofuran / 1.5 h / 20 °C 6.1: 63.2 mg / NaClO2; 2-methyl-2-butene; aq. citric acid/Na2HPO4 / 2-methyl-propan-2-ol / 1.5 h / 0 °C / pH 3.6 7.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 0.5 h / 0 °C 7.2: 74 percent / DMAP / tetrahydrofuran; toluene / 3 h 8.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 9.1: 38 percent / HF*pyridine / 168 h / 35 - 40 °C View Scheme

1.1: aq. AcOH / tetrahydrofuran / 3.5 h / 30 °C 2.1: 101 mg / TPAP; NMO; molecular sieves / CH2Cl2 / 0.33 h 3.1: LDA / tetrahydrofuran / 0.58 h / -78 - -40 °C 3.2: 86 percent / tetrahydrofuran / 1 h / -78 °C 4.1: 91 percent / pyridine / CH2Cl2 / 2 h 5.1: 86 percent / OsO4; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 18 h / 20 °C 6.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0 °C 7.1: HF*pyridine / tetrahydrofuran / 1.5 h / 20 °C 8.1: 63.2 mg / NaClO2; 2-methyl-2-butene; aq. citric acid/Na2HPO4 / 2-methyl-propan-2-ol / 1.5 h / 0 °C / pH 3.6 9.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 0.5 h / 0 °C 9.2: 74 percent / DMAP / tetrahydrofuran; toluene / 3 h 10.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 11.1: 38 percent / HF*pyridine / 168 h / 35 - 40 °C View Scheme

1.1: NEt3; SOCl2 / CH2Cl2 / 0.33 h / 0 °C 2.1: 122 mg / BuNF*3H2O / tetrahydrofuran / 2 h / Heating 3.1: 75 percent / Et3N; DMAP / CH2Cl2 / 0 - 20 °C 4.1: aq. AcOH / tetrahydrofuran / 3.5 h / 30 °C 5.1: 101 mg / TPAP; NMO; molecular sieves / CH2Cl2 / 0.33 h 6.1: LDA / tetrahydrofuran / 0.58 h / -78 - -40 °C 6.2: 86 percent / tetrahydrofuran / 1 h / -78 °C 7.1: 91 percent / pyridine / CH2Cl2 / 2 h 8.1: 86 percent / OsO4; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 18 h / 20 °C 9.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0 °C 10.1: HF*pyridine / tetrahydrofuran / 1.5 h / 20 °C 11.1: 63.2 mg / NaClO2; 2-methyl-2-butene; aq. citric acid/Na2HPO4 / 2-methyl-propan-2-ol / 1.5 h / 0 °C / pH 3.6 12.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 0.5 h / 0 °C 12.2: 74 percent / DMAP / tetrahydrofuran; toluene / 3 h 13.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 14.1: 38 percent / HF*pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 63.2 mg / NaClO2; 2-methyl-2-butene; aq. citric acid/Na2HPO4 / 2-methyl-propan-2-ol / 1.5 h / 0 °C / pH 3.6 2.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 0.5 h / 0 °C 2.2: 74 percent / DMAP / tetrahydrofuran; toluene / 3 h 3.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 4.1: 38 percent / HF*pyridine / 168 h / 35 - 40 °C View Scheme

1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 2: 38 percent / HF*pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 91 percent / pyridine / CH2Cl2 / 2 h 2.1: 86 percent / OsO4; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 18 h / 20 °C 3.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0 °C 4.1: HF*pyridine / tetrahydrofuran / 1.5 h / 20 °C 5.1: 63.2 mg / NaClO2; 2-methyl-2-butene; aq. citric acid/Na2HPO4 / 2-methyl-propan-2-ol / 1.5 h / 0 °C / pH 3.6 6.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 0.5 h / 0 °C 6.2: 74 percent / DMAP / tetrahydrofuran; toluene / 3 h 7.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 8.1: 38 percent / HF*pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 0.5 h / 0 °C 1.2: 74 percent / DMAP / tetrahydrofuran; toluene / 3 h 2.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 3.1: 38 percent / HF*pyridine / 168 h / 35 - 40 °C View Scheme

1.1: HF*pyridine / tetrahydrofuran / 1.5 h / 20 °C 2.1: 63.2 mg / NaClO2; 2-methyl-2-butene; aq. citric acid/Na2HPO4 / 2-methyl-propan-2-ol / 1.5 h / 0 °C / pH 3.6 3.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 0.5 h / 0 °C 3.2: 74 percent / DMAP / tetrahydrofuran; toluene / 3 h 4.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 5.1: 38 percent / HF*pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 86 percent / OsO4; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 18 h / 20 °C 2.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0 °C 3.1: HF*pyridine / tetrahydrofuran / 1.5 h / 20 °C 4.1: 63.2 mg / NaClO2; 2-methyl-2-butene; aq. citric acid/Na2HPO4 / 2-methyl-propan-2-ol / 1.5 h / 0 °C / pH 3.6 5.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 0.5 h / 0 °C 5.2: 74 percent / DMAP / tetrahydrofuran; toluene / 3 h 6.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 7.1: 38 percent / HF*pyridine / 168 h / 35 - 40 °C View Scheme