1: With tetrachloromethane; triphenylphosphine in tetrahydrofuran T=20°C; 2: With silica gel

1.1: 96 percent / NaH / dimethylformamide / 20 °C 2.1: nBuLi 2.2: 89 percent / tetrahydrofuran / 0 °C 3.1: nBuLi 3.2: 95 percent / tetrahydrofuran / 0 °C 4.1: 100 percent / CSA; MeOH / 60 °C 5.1: 100 percent / DMAP; Et3N / dimethylformamide / 20 °C 6.1: 78 percent / DIBAL-H / toluene / -78 °C 7.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 8.1: 65 percent / NaH / CH2Cl2 / 20 °C 9.1: 100 percent / TBAF / tetrahydrofuran / 0 °C 10.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 11.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 12.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 13.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 14.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 14.2: 43 percent / silica gel View Scheme

1.1: 84 percent / Br2 / CHCl3 / 20 °C 2.1: 80 percent / K2CO3 / dimethylformamide / 20 °C 3.1: 73 percent / 160 °C 4.1: 87 percent / K2CO3 / dimethylformamide / 20 °C 5.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 6.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 7.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 8.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 9.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 10.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 10.2: 43 percent / silica gel View Scheme

1.1: mCPBA / CH2Cl2 / 20 °C 2.1: HCl / methanol / 20 °C 3.1: 84 percent / Br2 / CHCl3 / 20 °C 4.1: 80 percent / K2CO3 / dimethylformamide / 20 °C 5.1: 73 percent / 160 °C 6.1: 87 percent / K2CO3 / dimethylformamide / 20 °C 7.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 8.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 9.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 10.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 11.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 12.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 12.2: 43 percent / silica gel View Scheme

1.1: nBuLi 1.2: 89 percent / tetrahydrofuran / 0 °C 2.1: nBuLi 2.2: 95 percent / tetrahydrofuran / 0 °C 3.1: 100 percent / CSA; MeOH / 60 °C 4.1: 100 percent / DMAP; Et3N / dimethylformamide / 20 °C 5.1: 78 percent / DIBAL-H / toluene / -78 °C 6.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 7.1: 65 percent / NaH / CH2Cl2 / 20 °C 8.1: 100 percent / TBAF / tetrahydrofuran / 0 °C 9.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 10.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 11.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 12.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 13.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 13.2: 43 percent / silica gel View Scheme

1.1: 96 percent / K2CO3 / dimethylformamide / 20 °C 2.1: mCPBA / CH2Cl2 / 20 °C 3.1: HCl / methanol / 20 °C 4.1: 84 percent / Br2 / CHCl3 / 20 °C 5.1: 80 percent / K2CO3 / dimethylformamide / 20 °C 6.1: 73 percent / 160 °C 7.1: 87 percent / K2CO3 / dimethylformamide / 20 °C 8.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 9.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 10.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 11.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 12.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 13.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 13.2: 43 percent / silica gel View Scheme

1.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 2.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 3.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 4.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 5.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 5.2: 43 percent / silica gel View Scheme

1.1: nBuLi 1.2: 95 percent / tetrahydrofuran / 0 °C 2.1: 100 percent / CSA; MeOH / 60 °C 3.1: 100 percent / DMAP; Et3N / dimethylformamide / 20 °C 4.1: 78 percent / DIBAL-H / toluene / -78 °C 5.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 6.1: 65 percent / NaH / CH2Cl2 / 20 °C 7.1: 100 percent / TBAF / tetrahydrofuran / 0 °C 8.1: 98 percent / K2CO3 / dimethylformamide / 20 °C 9.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 10.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 11.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 12.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 12.2: 43 percent / silica gel View Scheme

1.1: 80 percent / K2CO3 / dimethylformamide / 20 °C 2.1: 73 percent / 160 °C 3.1: 87 percent / K2CO3 / dimethylformamide / 20 °C 4.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 5.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 6.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 7.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 8.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 9.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 9.2: 43 percent / silica gel View Scheme

1.1: 73 percent / 160 °C 2.1: 87 percent / K2CO3 / dimethylformamide / 20 °C 3.1: 95 percent / OsO4; NaIO4 / H2O; diethyl ether / 20 °C 4.1: 72 percent / nBuLi / tetrahydrofuran / 0 °C 5.1: 49 percent / sBuLi / tetrahydrofuran / -78 °C 6.1: 76 percent / IBX / toluene; dimethylsulfoxide / 20 °C 7.1: 63 percent / HCO2NH4 / Pd/C / acetone / 20 °C 8.1: PPh3; CCl4 / tetrahydrofuran / 20 °C 8.2: 43 percent / silica gel View Scheme