1.1: 2,6-lutidine / CH2Cl2 / 12 h / -45 °C 2.1: 6.6 mg / aq. hydrogen peroxide; aq. Na2CO3 / ethyl acetate / 1 h / 20 °C 3.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 4.1: 97 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 0.08 h / 20 °C 5.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C 5.2: 89 percent / tetrahydrofuran / 1 h / -78 °C 6.1: 91 percent / tetrakis(triphenylphosphine)palladium / diethyl ether; tetrahydrofuran / 1 h / 20 °C 7.1: 88 percent / N-chlorosuccinimide / methanol / 10 h / 20 °C 8.1: 89 percent / pyridinium p-toluenesulfonate; 2-methoxypropene / CH2Cl2 / 0.05 h / 20 °C 9.1: 80 percent / lithium diisopropyl amide; MoO5*pyridine*HMPA / tetrahydrofuran / 0.92 h / -23 °C 10.1: 92 percent / DMAP / CH2Cl2 / 0.5 h / 20 °C 11.1: 68 percent / DBN / toluene / 10 h / Heating 12.1: 86 percent / OsO4; pyridine / diethyl ether; tetrahydrofuran / 18 h / 20 °C 13.1: 86 percent / DBU / toluene / 4 h / Heating 14.1: pyridinium p-toluenesulfonic acid / methanol / 0.5 h / 20 °C 15.1: 15 mg / DMAP; imidazole / dimethylformamide / 5 h / 20 °C 16.1: 97 percent / H2 / Pd(OH)2 / ethanol / 1 h / 20 °C 17.1: 94 percent / pyridine / CH2Cl2 / 1 h / -78 - 0 °C 18.1: 66 percent / DMAP / CH2Cl2 / 6 h / 20 °C 19.1: 83 percent / tetrahydrofuran / 0.33 h / -78 °C 20.1: 88 percent / HF*pyridine / tetrahydrofuran / 2 h / 20 °C 21.1: 94 percent / pyridine / CH2Cl2 / 3 h / 20 °C 22.1: 80 percent / TASF / tetrahydrofuran / 48 h / 20 °C 23.1: 77 percent / LHMDS / tetrahydrofuran / -78 - 0 °C 24.1: 84 percent / Zn; aq. AcOH / 16 h / 20 °C View Scheme

1.1: 2,6-lutidine / CH2Cl2 / 12 h / -45 °C 2.1: 6.6 mg / aq. hydrogen peroxide; aq. Na2CO3 / ethyl acetate / 1 h / 20 °C 3.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 4.1: 97 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 0.08 h / 20 °C 5.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C 5.2: 89 percent / tetrahydrofuran / 1 h / -78 °C 6.1: 91 percent / tetrakis(triphenylphosphine)palladium / diethyl ether; tetrahydrofuran / 1 h / 20 °C 7.1: 88 percent / N-chlorosuccinimide / methanol / 10 h / 20 °C 8.1: 89 percent / pyridinium p-toluenesulfonate; 2-methoxypropene / CH2Cl2 / 0.05 h / 20 °C 9.1: 80 percent / lithium diisopropyl amide; MoO5*pyridine*HMPA / tetrahydrofuran / 0.92 h / -23 °C 10.1: 92 percent / DMAP / CH2Cl2 / 0.5 h / 20 °C 11.1: 68 percent / DBN / toluene / 10 h / Heating 12.1: 86 percent / OsO4; pyridine / diethyl ether; tetrahydrofuran / 18 h / 20 °C 13.1: 86 percent / DBU / toluene / 4 h / Heating 14.1: pyridinium p-toluenesulfonic acid / methanol / 0.5 h / 20 °C 15.1: 15 mg / DMAP; imidazole / dimethylformamide / 5 h / 20 °C 16.1: 97 percent / H2 / Pd(OH)2 / ethanol / 1 h / 20 °C 17.1: 94 percent / pyridine / CH2Cl2 / 1 h / -78 - 0 °C 18.1: 66 percent / DMAP / CH2Cl2 / 6 h / 20 °C 19.1: 83 percent / tetrahydrofuran / 0.33 h / -78 °C 20.1: 88 percent / HF*pyridine / tetrahydrofuran / 2 h / 20 °C 21.1: 94 percent / pyridine / CH2Cl2 / 3 h / 20 °C 22.1: 80 percent / TASF / tetrahydrofuran / 48 h / 20 °C View Scheme