1.1: 68 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 8 h / 20 °C 2.1: 92 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C 3.1: 71 percent / Et3N / CH2Cl2 / 1 h / 0 °C 4.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 5.1: 81 percent / pyridine / 3 h / Heating 6.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 7.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 8.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 9.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 10.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 11.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 12.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 12.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 13.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 14.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 92 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C 2.1: 71 percent / Et3N / CH2Cl2 / 1 h / 0 °C 3.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 4.1: 81 percent / pyridine / 3 h / Heating 5.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 6.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 7.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 8.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 9.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 10.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 11.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 11.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 12.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 13.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 90 percent / I2; PPh3; imidazole / CH2Cl2 / 2 h / 20 °C 2.1: 95 percent / NaHCO3 / acetonitrile / 16 h / Heating 3.1: NaHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C 3.2: 76 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 - 20 °C 4.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 5.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 6.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 7.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 8.1: 81 percent / pyridine / 3 h / Heating 9.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 10.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 11.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 12.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 13.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 14.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 15.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 15.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 16.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 17.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 95 percent / NaHCO3 / acetonitrile / 16 h / Heating 2.1: NaHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C 2.2: 76 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 - 20 °C 3.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 4.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 5.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 6.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 7.1: 81 percent / pyridine / 3 h / Heating 8.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 9.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 10.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 11.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 12.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 13.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 14.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 14.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 15.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 16.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 2.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 3.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 4.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 5.1: 81 percent / pyridine / 3 h / Heating 6.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 7.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 8.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 9.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 10.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 11.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 12.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 12.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 13.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 14.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 99 percent / acetonitrile / 16 h / Heating 2.1: KN(SiMe3)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 °C 2.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 °C 3.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 4.1: KOH / H2O; methanol / 60 °C 5.1: 2.12 g / TsOH / CH2Cl2 / 0.5 h / 20 °C 6.1: 68 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 8 h / 20 °C 7.1: 92 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C 8.1: 71 percent / Et3N / CH2Cl2 / 1 h / 0 °C 9.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 10.1: 81 percent / pyridine / 3 h / Heating 11.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 12.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 13.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 14.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 15.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 16.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 17.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 17.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 18.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 19.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1.1: tetrahydrofuran / 2.5 h / -78 - 0 °C 1.2: 70 percent / HMPA / tetrahydrofuran / -78 - 20 °C 2.1: 74 percent / AcOH / H2O / 16 h / 100 °C 3.1: 78 percent / tetrahydrofuran / -20 °C 4.1: 88 percent / propionic acid / 2 h / Heating 5.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 6.1: KOH / H2O; methanol / 2 h / 60 °C 7.1: 1.5 g / TsOH / CH2Cl2 / 1 h / 20 °C 8.1: 95 percent / TsOH / acetone / 0.5 h / 20 °C 9.1: 95 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 12 h 10.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 11.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 12.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 13.1: 81 percent / pyridine / 3 h / Heating 14.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 15.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 16.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 17.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 18.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 19.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 20.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 20.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 21.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 22.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 78 percent / tetrahydrofuran / -20 °C 2.1: 88 percent / propionic acid / 2 h / Heating 3.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 4.1: KOH / H2O; methanol / 2 h / 60 °C 5.1: 1.5 g / TsOH / CH2Cl2 / 1 h / 20 °C 6.1: 95 percent / TsOH / acetone / 0.5 h / 20 °C 7.1: 95 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 12 h 8.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 9.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 10.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 11.1: 81 percent / pyridine / 3 h / Heating 12.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 13.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 14.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 15.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 16.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 17.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 18.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 18.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 19.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 20.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 74 percent / AcOH / H2O / 16 h / 100 °C 2.1: 78 percent / tetrahydrofuran / -20 °C 3.1: 88 percent / propionic acid / 2 h / Heating 4.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 5.1: KOH / H2O; methanol / 2 h / 60 °C 6.1: 1.5 g / TsOH / CH2Cl2 / 1 h / 20 °C 7.1: 95 percent / TsOH / acetone / 0.5 h / 20 °C 8.1: 95 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 12 h 9.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 10.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 11.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 12.1: 81 percent / pyridine / 3 h / Heating 13.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 14.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 15.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 16.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 17.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 18.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 19.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 19.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 20.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 21.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 9.95 g / p-TsOH / methanol; H2O / 1 h / 20 °C 2.1: 91 percent / I2; imidazole; PPh3 / toluene / 2 h / 20 °C 3.1: 99 percent / acetonitrile / 16 h / Heating 4.1: KN(SiMe3)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 °C 4.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 °C 5.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 6.1: KOH / H2O; methanol / 60 °C 7.1: 2.12 g / TsOH / CH2Cl2 / 0.5 h / 20 °C 8.1: 68 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 8 h / 20 °C 9.1: 92 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C 10.1: 71 percent / Et3N / CH2Cl2 / 1 h / 0 °C 11.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 12.1: 81 percent / pyridine / 3 h / Heating 13.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 14.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 15.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 16.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 17.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 18.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 19.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 19.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 20.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 21.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme