1.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 2.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 3.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 4.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 5.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 5.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 6.1: DMAP / pentane / 168 h / 20 °C 6.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 7.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 8.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 9.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 10.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 11.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 12.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 14.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 15.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 16.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 18.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 2.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 3.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 4.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 4.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 5.1: DMAP / pentane / 168 h / 20 °C 5.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 6.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 8.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 9.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 10.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 13.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 14.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 17.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 2.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 3.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 3.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 4.1: DMAP / pentane / 168 h / 20 °C 4.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 5.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 6.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 7.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 8.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 9.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 12.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 13.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 14.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 15.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 16.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 2.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 2.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3.1: DMAP / pentane / 168 h / 20 °C 3.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 4.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 5.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 6.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 7.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 8.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 9.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 11.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 12.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 13.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 15.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 2: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 3: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 4: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 5: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 6: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 7: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 8: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 9: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 10: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 12: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 2: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 3: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 4: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 5: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 6: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 7: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 8: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 9: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 11: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 2: 93 percent / PPTS / ethanol / 10 h / 50 °C 3: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 4: 19 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 5: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 6: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 7: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 8: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 9: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 11: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 2: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 3: 93 percent / PPTS / ethanol / 10 h / 50 °C 4: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5: 19 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 6: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 7: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 8: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 9: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 10: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 12: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1: 19 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 4: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 6: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 7: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 8: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2: 19 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 3: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 4: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 5: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 6: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 7: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 9: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme