1.1: 88 percent / propionic acid / 2 h / Heating 2.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 3.1: KOH / H2O; methanol / 2 h / 60 °C 4.1: 1.5 g / TsOH / CH2Cl2 / 1 h / 20 °C 5.1: 95 percent / TsOH / acetone / 0.5 h / 20 °C 6.1: 95 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 12 h 7.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 8.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 9.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °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: 75 percent / trifluoroacetylrhenium(VII) oxide; 2,6-lutidine / tetrahydrofuran / 8 h / 0 - 20 °C 2.1: 90 percent / Et3N / CH2Cl2 / 0.5 h / -30 °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: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 2.1: KOH / H2O; methanol / 2 h / 60 °C 3.1: 1.5 g / TsOH / CH2Cl2 / 1 h / 20 °C 4.1: 95 percent / TsOH / acetone / 0.5 h / 20 °C 5.1: 95 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 12 h 6.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 7.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 8.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 9.1: 81 percent / pyridine / 3 h / Heating 10.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 11.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 12.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 13.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 14.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 15.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 16.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 16.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 17.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 18.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 90 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 2.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 3.1: 81 percent / pyridine / 3 h / Heating 4.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 5.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 6.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 7.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 8.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 9.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 10.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 10.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 11.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 12.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 2.1: 81 percent / pyridine / 3 h / Heating 3.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 4.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 5.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 6.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 7.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 8.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 9.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 9.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 10.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 11.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: 75 percent / trifluoroacetylrhenium(VII) oxide; 2,6-lutidine / tetrahydrofuran / 8 h / 0 - 20 °C 3.1: 90 percent / Et3N / CH2Cl2 / 0.5 h / -30 °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: 98 percent / H2 / Rh-Al2O3 / ethyl acetate / 12 h 2: 97 percent / I2, Ph3P, imidazole / CH2Cl2; benzene / 1 h 3: 91 percent / tetrahydrofuran / 12 h / 0 °C 4: 100 percent / (DHQD)2AQN, K2Fe3(CN)6, K2CO3, K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 12 h / 0 °C 5: 19 percent / pyridine / 10 h / Ambient temperature 6: 79 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 7: 1.) BF3*OEt2 / 1.) THF, -78 deg C, 10 min, 2.) THF, 20 min 8: i-Pr2NEt / CH2Cl2 / 12 h / Ambient temperature 9: TBAF / tetrahydrofuran / 6 h / 40 °C 10: 2,6-lutidine / tetrahydrofuran / 0.33 h 11: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 12: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, DMSO, 40 deg C, 30 min, 2.) THF, room temperature, 1 h 2: 86 percent / LiBEt3H / tetrahydrofuran / 12 h / 0 °C 3: 98 percent / H2 / Rh-Al2O3 / ethyl acetate / 12 h 4: 97 percent / I2, Ph3P, imidazole / CH2Cl2; benzene / 1 h 5: 91 percent / tetrahydrofuran / 12 h / 0 °C 6: 100 percent / (DHQD)2AQN, K2Fe3(CN)6, K2CO3, K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 12 h / 0 °C 7: 19 percent / pyridine / 10 h / Ambient temperature 8: 79 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 9: 1.) BF3*OEt2 / 1.) THF, -78 deg C, 10 min, 2.) THF, 20 min 10: i-Pr2NEt / CH2Cl2 / 12 h / Ambient temperature 11: TBAF / tetrahydrofuran / 6 h / 40 °C 12: 2,6-lutidine / tetrahydrofuran / 0.33 h 13: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 14: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme

1: 86 percent / LiBEt3H / tetrahydrofuran / 12 h / 0 °C 2: 98 percent / H2 / Rh-Al2O3 / ethyl acetate / 12 h 3: 97 percent / I2, Ph3P, imidazole / CH2Cl2; benzene / 1 h 4: 91 percent / tetrahydrofuran / 12 h / 0 °C 5: 100 percent / (DHQD)2AQN, K2Fe3(CN)6, K2CO3, K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 12 h / 0 °C 6: 19 percent / pyridine / 10 h / Ambient temperature 7: 79 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 8: 1.) BF3*OEt2 / 1.) THF, -78 deg C, 10 min, 2.) THF, 20 min 9: i-Pr2NEt / CH2Cl2 / 12 h / Ambient temperature 10: TBAF / tetrahydrofuran / 6 h / 40 °C 11: 2,6-lutidine / tetrahydrofuran / 0.33 h 12: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 13: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme

1: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 deg C -> r.t. 2: I2, PPh3, imidazole / CH2Cl2 / 0.5 h / Ambient temperature 3: NaHCO3 / acetonitrile / 16 h / Heating 4: 62 percent / n-BuLi / tetrahydrofuran / 0.5 h 5: H2 / Rh(PPh3)3Cl / ethanol; benzene / 2 h / Ambient temperature 6: BF3*Et2O, Me2S / CH2Cl2 / 0.5 h / 0 deg C -> r.t. View Scheme