1.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C 2.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C 3.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 3.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 4.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 5.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 6.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 7.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 8.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 9.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 10.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme

1.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 1.2: 93 percent / tetrahydrofuran / 1 h / -78 °C 2.1: 65 percent / Na2HPO4; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C 3.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C 4.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C 5.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 5.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 6.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 7.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 8.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 9.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 10.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 11.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 12.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C 2.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 2.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 3.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 4.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 5.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 6.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 7.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 8.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 9.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme

1.1: pentane / 4 h / 0 °C 1.2: 97 percent / MeOH / 1 h / 20 °C 2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C 3.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 3.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 4.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 5.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 6.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 7.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 8.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 9.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 10.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme

1.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 1.2: 93 percent / tetrahydrofuran / 1 h / -78 °C 2.1: 65 percent / Na2HPO4; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C 3.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C 4.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C 5.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 5.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 6.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 7.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 8.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 9.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 10.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 11.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 12.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme

1.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C 2.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 3.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 3.2: 93 percent / tetrahydrofuran / 1 h / -78 °C 4.1: 65 percent / Na2HPO4; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C 5.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C 6.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C 7.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 7.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 8.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 9.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 10.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 11.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 12.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 13.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 14.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme

1.1: 65 percent / Na2HPO4; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C 2.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C 3.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C 4.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 4.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 5.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 6.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 7.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 8.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 9.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 10.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 11.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme

1.1: 96 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 2.1: pentane / 4 h / 0 °C 2.2: 97 percent / MeOH / 1 h / 20 °C 3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.2: 85 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C 4.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 4.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 5.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 6.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 7.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 8.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 9.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 10.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 11.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme

1.1: Dess-Martin periodane / dichloromethane / 0.67 h / 20 °C / |Inert atmosphere 2.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / |Inert atmosphere 2.2: 1 h / -78 °C / |Inert atmosphere 2.3: 3 h / -78 - 20 °C / |Inert atmosphere 3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / |Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 5.2: 20 °C / |Inert atmosphere 6.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / |Inert atmosphere View Scheme

1.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / |Inert atmosphere 1.2: 1 h / -78 °C / |Inert atmosphere 1.3: 3 h / -78 - 20 °C / |Inert atmosphere 2.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / |Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 4.2: 20 °C / |Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / |Inert atmosphere View Scheme