1: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 2: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 3: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 4: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 6: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C View Scheme

1: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 2: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 3: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 4: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 6: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 7: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 8: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 9: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 10: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 11: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 12: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C View Scheme

1: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 2: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 3: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 4: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 6: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 7: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 8: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 9: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature View Scheme

1: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 2: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 3: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 4: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 6: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 7: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 8: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 9: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 10: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 11: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 12: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 13: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 14: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C View Scheme

1: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 2: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 3: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 4: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 6: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 7: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 8: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 9: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 10: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 11: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 12: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 13: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 14: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C 15: pyridine / 2 h / 20 - 25 °C View Scheme

1: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 2: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 3: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 4: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 6: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 7: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 8: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 9: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 10: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 11: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 12: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 13: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 14: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C View Scheme

1: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 2: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 3: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 4: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 6: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C 7: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 8: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 9: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 10: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 11: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 12: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 13: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C View Scheme

1: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 2: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h View Scheme

1.1: n-BuLi / heptane; hexane / 1.75 h / 0 °C 1.2: 66 percent / heptane; hexane / 2 h / 0 °C 2.1: 99 percent / aq. trifluoroacetic acid / 4 h / 40 °C 3.1: 85 percent / sodium borohydride / aq. methanol / 0.33 h / 0 °C 4.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C 4.2: 90 percent / tetrahydrofuran / 8 h / 20 °C 5.1: 89 percent / potassium acetate; palladium acetate; 1,3-bis(diphenylphosphino)propane / dimethylformamide / 25 h / 85 °C / 775.72 Torr 6.1: 97 percent / sodium iodide; trimethylsilyl chloride / acetonitrile / 24 h / 20 °C 7.1: 85 percent / cesium carbonate / dimethylsulfoxide / 3 h / 65 °C 8.1: 73 percent / trifluoroacetic acid / toluene / 24 h / 75 °C 9.1: 80 percent / acetic acid / 4 h / 100 °C 10.1: 88 percent / tetra-n-butylammonium iodide; boron tribromide / CH2Cl2 / 0.5 h / -40 °C 11.1: 62 percent / pyridinium chlorochromate; celite; isopropyl alcohol / CH2Cl2 / 1 h / 20 °C View Scheme