1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 2: 95 percent / benzene / 3 h / Heating 3: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C 4: 83 percent / Ph3P, CCl4 / 24 h / 100 °C 5: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C 6: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C 7: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 8: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 9: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 10: 82 percent / DIBAL / toluene / 1 h / -78 °C 11: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 12: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 13: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C View Scheme

1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 2: 95 percent / benzene / 3 h / Heating 3: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C 4: 83 percent / Ph3P, CCl4 / 24 h / 100 °C 5: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C 6: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C 7: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 8: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 9: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 10: 82 percent / DIBAL / toluene / 1 h / -78 °C 11: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 12: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 13: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C 14: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, -78 deg C -> 0 deg C, 30 min 15: 90 percent / NaClO2, isobutylene, NaH2PO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1 h / Ambient temperature 16: 73 percent / TBAF / tetrahydrofuran / 8 h / 25 °C 17: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-DMAP / 1) THF, 25 deg C, 15 min, 2) toluene, 25 deg C, 12 h 18: 91 percent / CF3CO2H / CH2Cl2 / 1) -20 deg C -> 0 deg C, 2) 0 deg C, 1 h 19: Na2EDTA, 1,1,1-trifluoroacetone, Oxone, NaHCO3 / acetonitrile; H2O / 0 °C View Scheme

1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 2: 95 percent / benzene / 3 h / Heating 3: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C 4: 83 percent / Ph3P, CCl4 / 24 h / 100 °C 5: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C 6: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C 7: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 8: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 9: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 10: 82 percent / DIBAL / toluene / 1 h / -78 °C 11: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 12: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 13: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C 14: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, -78 deg C -> 0 deg C, 30 min 15: 90 percent / NaClO2, isobutylene, NaH2PO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1 h / Ambient temperature 16: 73 percent / TBAF / tetrahydrofuran / 8 h / 25 °C 17: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-DMAP / 1) THF, 25 deg C, 15 min, 2) toluene, 25 deg C, 12 h 18: 91 percent / CF3CO2H / CH2Cl2 / 1) -20 deg C -> 0 deg C, 2) 0 deg C, 1 h View Scheme

1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 2: 95 percent / benzene / 3 h / Heating 3: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C 4: 83 percent / Ph3P, CCl4 / 24 h / 100 °C 5: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C 6: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C 7: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 8: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 9: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 10: 82 percent / DIBAL / toluene / 1 h / -78 °C 11: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 12: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C View Scheme

1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 2: 95 percent / benzene / 3 h / Heating 3: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C 4: 83 percent / Ph3P, CCl4 / 24 h / 100 °C 5: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C 6: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C 7: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 8: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 9: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 10: 82 percent / DIBAL / toluene / 1 h / -78 °C 11: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 12: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 13: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C 14: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, -78 deg C -> 0 deg C, 30 min 15: 90 percent / NaClO2, isobutylene, NaH2PO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 2: 95 percent / benzene / 3 h / Heating 3: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C 4: 83 percent / Ph3P, CCl4 / 24 h / 100 °C 5: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C 6: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C 7: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 8: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 9: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 10: 82 percent / DIBAL / toluene / 1 h / -78 °C 11: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min View Scheme

1.1: 5.56 g / Pb(OAc)4 / ethyl acetate / 2 h / 0 °C 2.1: 68 percent / PPh3 / CH2Cl2 / 0.25 h / -60 °C 3.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 3.2: 65 percent / tetrahydrofuran / 6 h / -78 - 20 °C 4.1: 74 percent / 4 Angstroem molecular sieves; TBAF*3H2O / tetrahydrofuran / 3 h 5.1: 81 percent / DCC; DMAP / CH2Cl2 / 14 h / 20 °C 6.1: 80 percent / CH2Cl2 / [Mo{(t-Bu)(3,5-dimethylphenyl)N}3] / toluene / 8 h / 80 °C 7.1: 99 percent / quinoline; H2 / Lindlar catalyst / hexane; CH2Cl2 / 8 h / 20 °C 8.1: 79 percent / aq. HF / acetonitrile; diethyl ether / 8 h / 20 °C View Scheme