1: 1.) Ph3P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h 2: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C 3: LDA, DABCO / tetrahydrofuran; hexane / 48 h / -78 °C 4: Bu4N+F- / tetrahydrofuran / 24 h / 15 °C 5: 70 percent / Li, EtNH2 / tetrahydrofuran / 3.5 h / -78 °C 6: 49 percent / SOCl2, pyridine / 3 h / 15 °C 7: 92 percent / MnO2 / hexane / 12 h / 15 °C 8: 65 percent / 67 percent aq. Ca(ClO)2, glacial acetic acid / acetonitrile / 20 h / 15 °C View Scheme

1: 1.) Ph3P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h 2: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C 3: LDA, DABCO / tetrahydrofuran; hexane / 48 h / -78 °C 4: Bu4N+F- / tetrahydrofuran / 24 h / 15 °C 5: 70 percent / Li, EtNH2 / tetrahydrofuran / 3.5 h / -78 °C 6: 49 percent / SOCl2, pyridine / 3 h / 15 °C 7: 92 percent / MnO2 / hexane / 12 h / 15 °C View Scheme

1: 1.) Ph3P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h 2: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C 3: LDA, DABCO / tetrahydrofuran; hexane / 48 h / -78 °C 4: Bu4N+F- / tetrahydrofuran / 24 h / 15 °C 5: 70 percent / Li, EtNH2 / tetrahydrofuran / 3.5 h / -78 °C View Scheme