1: 1) 20percent diisobutylaluminum hydride / 1) ether, toluene, -80 deg C, 10 h, 2) ether, 12 h, reflux 2: 98 percent / H2 / PtO2 / methanol; toluene / 6 h View Scheme

n-butyllithium in tetrahydrofuran T=-30°C;

n-butyllithium 2) ether, hexane, 1.5 h, room temperature; Multistep reaction;