1: 89 percent / NaH, 15-crown-5 2: 95 percent / HOAc / tetrahydrofuran; H2O 3: 99 percent / imidazole / dimethylformamide 4: 72 percent / DIBAL / tetrahydrofuran / -78 - 0 °C 5: 88 percent 6: 1.) LiHMDS / 1.) THF, -78 deg C to 0 deg C, 2.) THF, -78 deg C to 0 deg C 7: 78 percent 8: 77 percent / Dess-Martin periodinane, pyridine / CH2Cl2 / Ambient temperature 9: 80 percent / aq. HF / acetonitrile / Ambient temperature 10: 85 percent / Et3N 11: 1.) Bu3SnH, AIBN, 2.) I2 / 1.) benzene, 90 deg C, 1 h, 2.) CH2Cl2, 0 deg C 12: 56 percent / LiI / pyridine / 16 h / 130 °C 13: 1.) EDS, DMAP, DMAP*HCl, 2.) i-Pr2NEt, <(2-furyl)3P>2PdCl2 / 1.) CH2Cl2, room temperature, 5 h, 2.) THF, DMF, room temperature, 7 h 14: 90 percent / TBAF, AcOH / tetrahydrofuran / 3 h / 0 °C 15: 71 percent / HF*pyr, pyridine / tetrahydrofuran / Ambient temperature View Scheme