1: 98 percent / benzene / 2 h / Heating 2: 74 percent / diethyl ether; pentane / 1 h / -100 °C 3: 99 percent / imidazole / dimethylformamide / 1) 0 deg C, 45 min, 2) 25 deg C, 2.5 h 4: 95 percent / 4-methylmorpholine N-oxide, OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 1) 0 deg C, 2.5 h, 2) 25 deg C, 12 h 5: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 6: 95 percent / benzene / 3 h / Heating 7: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C 8: 83 percent / Ph3P, CCl4 / 24 h / 100 °C 9: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C 10: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C 11: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 12: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 13: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 14: 82 percent / DIBAL / toluene / 1 h / -78 °C 15: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 16: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 17: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C View Scheme

1: 74 percent / diethyl ether / 0.5 h / -100 °C 2: 98 percent / 2,6-lutidine / CH2Cl2 / 0.75 h / -78 °C 3: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 4: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min 5: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h 6: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 7: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 8: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C View Scheme

1: 98 percent / 2,6-lutidine / CH2Cl2 / 0.75 h / -78 °C 2: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 3: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min 4: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h 5: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 6: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 7: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C View Scheme

1: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 2: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min 3: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h 4: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 5: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 6: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C View Scheme

1: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min 2: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h 3: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 4: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 5: 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 View Scheme

1: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h 2: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 3: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 4: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C View Scheme

1: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C 2: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 3: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 4: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 5: 82 percent / DIBAL / toluene / 1 h / -78 °C 6: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 7: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 8: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C View Scheme

1: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 2: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 3: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 4: 82 percent / DIBAL / toluene / 1 h / -78 °C 5: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 6: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 7: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C View Scheme

1: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 2: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 3: 82 percent / DIBAL / toluene / 1 h / -78 °C 4: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 5: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 6: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C View Scheme