1: 70 percent / O3, PPh3 / CH2Cl2 / -78 °C 2: 75 percent / n-BuLi / tetrahydrofuran / -78 °C 3: 87 percent / HF, splinters of glass / acetonitrile / 0 °C 4: 78 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / Ambient temperature 5: 83 percent / NaNH2 / tetrahydrofuran / 0.33 h / Ambient temperature 6: 99 percent / TBAF, 4 Angstroem molecular sieves / tetrahydrofuran / -78 °C 7: 80 percent / DCC, 4-DMAP / CH2Cl2 / 12 h / Ambient temperature 8: 94 percent / <RuCHPh>Cl2*(PCy3)2 / CH2Cl2 / 12 h / Ambient temperature 9: 65 percent / HF / acetonitrile; diethyl ether / 12 h / Ambient temperature 10: 48 percent / dimethyl dioxirane / CH2Cl2 / 2 h / -35 °C View Scheme

1: 70 percent / O3, PPh3 / CH2Cl2 / -78 °C 2: 75 percent / n-BuLi / tetrahydrofuran / -78 °C 3: 87 percent / HF, splinters of glass / acetonitrile / 0 °C 4: 78 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / Ambient temperature 5: 83 percent / NaNH2 / tetrahydrofuran / 0.33 h / Ambient temperature 6: 99 percent / TBAF, 4 Angstroem molecular sieves / tetrahydrofuran / -78 °C View Scheme