1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 2: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

1.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °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: 76 percent / lithium hydroxide; hydrogen peroxide / tetrahydrofuran; H2O / 4 h / 20 °C 2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 2.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 3.1: pyridine / CH2Cl2 / 1 h / 0 °C 4.1: CH2Cl2 / 5 h / 20 °C 5.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 6.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 7.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 8.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 9.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

1.1: 77 percent / Et3N 2.1: LDA 3.1: 88 percent / CSA / methanol 4.1: PCC 4.2: 90 percent / NaClO2 5.1: 73 percent / TBAF 6.1: 77 percent / TCBCl; DIEA; DMAP 7.1: 59 percent / HF*pyr View Scheme

1.1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C 2.1: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C 3.1: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C 4.1: 80 percent / PCC 5.1: LDA 6.1: 88 percent / CSA / methanol 7.1: PCC 7.2: 90 percent / NaClO2 8.1: 73 percent / TBAF 9.1: 77 percent / TCBCl; DIEA; DMAP 10.1: 59 percent / HF*pyr View Scheme

1.1: 77 percent / Et3N 2.1: LDA 3.1: 88 percent / CSA / methanol 4.1: PCC 4.2: 90 percent / NaClO2 5.1: 73 percent / TBAF 6.1: 77 percent / TCBCl; DIEA; DMAP 7.1: 59 percent / HF*pyr View Scheme

1.1: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C 2.1: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C 3.1: 80 percent / PCC 4.1: LDA 5.1: 88 percent / CSA / methanol 6.1: PCC 6.2: 90 percent / NaClO2 7.1: 73 percent / TBAF 8.1: 77 percent / TCBCl; DIEA; DMAP 9.1: 59 percent / HF*pyr View Scheme

1.1: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C 2.1: 80 percent / PCC 3.1: LDA 4.1: 88 percent / CSA / methanol 5.1: PCC 5.2: 90 percent / NaClO2 6.1: 73 percent / TBAF 7.1: 77 percent / TCBCl; DIEA; DMAP 8.1: 59 percent / HF*pyr View Scheme

1.1: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - 20 °C 2.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h 2.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C 4.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 5.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 5.2: 93 percent / tetrahydrofuran / 1 h / -78 °C 6.1: 65 percent / Na2HPO4; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C 7.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C 8.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C 9.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 9.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 10.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 11.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 12.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 13.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 14.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 15.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 16.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme

1.1: 10.95 g / LiHMDS / tetrahydrofuran / 0.67 h / 55 °C 2.1: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - 20 °C 3.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h 3.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C 4.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C 5.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 6.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 6.2: 93 percent / tetrahydrofuran / 1 h / -78 °C 7.1: 65 percent / Na2HPO4; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C 8.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C 9.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C 10.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 10.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 11.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 12.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 13.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 14.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 15.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 16.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 17.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme