1: 70 percent / DIBAL / -78 °C 2: 1.) Im.; 2.) Raney Ni 3: 98 percent / LDA / tetrahydrofuran 4: 81 percent / DIBAL 5: 1.) TBAF; 2.) Raney Ni View Scheme

1.1: 87 percent / DIBALH; ZnBr2 / tetrahydrofuran; heptane / 0.5 h / -78 °C 2.1: 93 percent / AlMe3 / CH2Cl2 / 4 h / Heating 3.1: 71 percent / tetrahydrofuran; diethyl ether / 50 °C 4.1: 92 percent / Et3SiH; TMSOTf / CH2Cl2 / 0.25 h / 0 °C 5.1: TFAA; 2,4,6-collidine / acetonitrile / 0.17 h / 0 °C 6.1: aq. K2CO3 / acetonitrile / 0.5 h / 20 °C 6.2: aq. NaBH4 / acetonitrile / 1 h / 20 °C 7.1: 81 percent / 4 Angstroem molecular sieves; Celite; PCC / CH2Cl2 / 3 h / 20 °C 8.1: 96 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 9.1: 93 percent / H2 / Pd/Al2O3 / tetrahydrofuran / 4 h / 20 °C / 37503 Torr View Scheme