1: Br2 / CCl4 2: 67 percent / Li2CO3, LiBr / dimethylformamide 3: tetrahydrofuran 4: LiN(iPr)2 / tetrahydrofuran 5: LiCl, methanesulfonyl chloride / dimethylformamide 6: K2CO3, CuI, Bu4NBr / dimethylformamide 7: 90 percent / H2 / Lindlar catalyst 8: 83 percent / Bu4NF, H2O / tetrahydrofuran 9: Dess-Martin periodinane, NaOAc / CH2Cl2 10: TiCl3*DME1.5, Zn-Cu / 1,2-dimethoxy-ethane / 36 h / 0 °C 11: 1.) MsCl, pyridine 2.) Bu4NOH / 1.) ether; 2.) THF 12: LiN(iPr)2 / tetrahydrofuran 13: 84 percent / Dess-Martin periodinane View Scheme