1.1: 57 percent / tetrahydrofuran; hexamethylphosphoric acid triamide 2.1: n-BuLi / tetrahydrofuran 2.2: 94 percent / NH4Cl / tetrahydrofuran 3.1: 91 percent / pyridine / CH2Cl2 4.1: 77 percent / Na/Hg / tetrahydrofuran; methanol / -30 °C 5.1: 88 percent / TBAF / tetrahydrofuran 6.1: 99 percent / I2; PPh3; imidazole / benzene 7.1: 88 percent / dimethylformamide 8.1: 82 percent / DIBAL-H / CH2Cl2 / -78 °C View Scheme

1: 1.) LDA, HMPA / 1.) THF, 0 deg C, 2 h; 2.) THF 2: 1.) NaBH4; 2.) LiAlH4 / 1.) MeOH; 2.) Et2O View Scheme

lithium diisopropyl amide in tetrahydrofuran T=-78°C; 3 h; Inert atmosphere;