1: 94 percent / HOAc / tetrahydrofuran; H2O / 36 h / Ambient temperature 2: 91 percent / imidazole / dimethylformamide / 16 h / Ambient temperature 3: 90 percent / DIBAL / tetrahydrofuran / 0.5 h / -78 °C 4: 89 percent / (COCl)2, DMSO, i-Pr2NEt / CH2Cl2 / 0.25 h / 0 °C 5: 1.) LiHMDS / 1.) THF, -78 deg C, 15 min; 0 deg C, 15 min, 2.) THF, -78 deg C, 30 min 6: 87 percent / diethyl ether / 1.) 0 deg C to room temperature, 3 h, 2.) room temperature, 16 h 7: 76 percent / Dess-Martin periodinane, pyridine / CH2Cl2 / 2 h / Ambient temperature; 1.) 0 deg C to room temperature, 3 h, 2.) room temperature, 16 h 8: 80 percent / aq. HF / acetonitrile / 4 h / Ambient temperature 9: 99 percent / 2,6-lutidine, Et3N / CH2Cl2 / 5 h / -78 °C 10: 1.) Bu3SnH, AIBN, 2.) I2 / 1.) benzene, 90 deg C, 1 h, 2.) CH2Cl2, 0 deg C 11: 56 percent / LiI / pyridine / 16 h / 130 °C 12: 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 13: 90 percent / TBAF, AcOH / tetrahydrofuran / 3 h / 0 °C 14: 71 percent / HF*pyr, pyridine / tetrahydrofuran / Ambient temperature View Scheme