T=200°C; Hydrogenation;

T=200°C; Hydrogenation;

T=200°C; Hydrogenation;

1: O3 / ethanol / -78 °C 2: NaBH4 / tetrahydrofuran; ethanol 3: imidazole / dimethylformamide 4: Br2 / CCl4 5: 67 percent / Li2CO3, LiBr / dimethylformamide 6: tetrahydrofuran 7: LiN(iPr)2 / tetrahydrofuran 8: LiCl, methanesulfonyl chloride / dimethylformamide 9: K2CO3, CuI, Bu4NBr / dimethylformamide 10: 90 percent / H2 / Lindlar catalyst 11: 83 percent / Bu4NF, H2O / tetrahydrofuran 12: Dess-Martin periodinane, NaOAc / CH2Cl2 13: TiCl3*DME1.5, Zn-Cu / 1,2-dimethoxy-ethane / 36 h / 0 °C 14: 1.) MsCl, pyridine 2.) Bu4NOH / 1.) ether; 2.) THF 15: LiN(iPr)2 / tetrahydrofuran 16: 84 percent / Dess-Martin periodinane View Scheme