1: 87 percent / Zn / aq. ethanol / 22 h / Heating 2: 67 percent / PPh3, DEAD / benzene / 15 h / 25 °C 3: 80 percent / NaH / methanol / 2 h / 5 °C 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) 0 deg C, 10 min 5: n-BuLi / diethyl ether; hexane / 1.) -78 deg C, 30 min, 2.) 25 deg C, 4.5 h 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) 5 deg C, 30 min 7: 51 percent / SmI2 / tetrahydrofuran; methanol / 0.33 h / -78 °C 8: 91 percent / K2CO3 / methanol / 2.5 h / 60 °C 9: 79 percent / TMSBr / CH2Cl2 / 1.) -30 deg C, 5 min, 2.) 3 deg C, 30 min 10: 100 percent / TBAF / tetrahydrofuran / 5.5 h / 25 °C 11: 80 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 25 °C 12: 86 percent / molecular sieves 4 Angstroem / toluene / 1.) -78 deg C, 2 h, 2.) -78 deg C to r.t. 13: 85 percent / t-BuOOH / VO(acac)2 / CH2Cl2 / 7 h / 25 °C 14: 92 percent / Et3N, DMAP / CH2Cl2 / 2.5 h / 3 °C 15: 90 percent / LiEt3BH / tetrahydrofuran / 1 h / 3 °C 16: 95 percent / PDC, molecular sieves 3 Angstroem / CH2Cl2 / 1 h / 25 °C 17: Et3N / CH2Cl2 / 1 h / 3 °C 18: TiCl4 / CH2Cl2 / 3 h / -78 - -15 °C 19: aq. HF / acetonitrile / 2 h / Ambient temperature 20: 72 percent / O2, CuCl, H2O / PdCl2 / dimethylformamide / 15 h / 25 °C 21: 41 percent / TESOTf, 2,6-lutidine / CH2Cl2 / 4 h / 25 °C View Scheme