1: 60 percent / pyridine / tetrahydrofuran / 1.) -30 deg C, 1 h, 2.) 0 deg C, 16 h 2: LiBr / acetone / 2 h / Heating 3: tetrahydrofuran / Heating 4: LDA / tetrahydrofuran / -78 °C 5: Li(sec-Bu)3BH / tetrahydrofuran / -10 °C 6: hexamethylphosphoric acid triamide / 1 h / 110 °C 7: Bu3SnH, AIBN / toluene / 1 h / 60 °C View Scheme

Multi-step reaction with 3 steps 1: 95 percent / N-chlorosuccinimide; K2CO3; N-tert-butylbenzenesulfenamide / CH2Cl2 / 3 h / 20 °C2: 75 percent / diethyl ether / 0.5 h / -78 °C3: 90 percent / H2 / Pd/C / acetic acid / 15 h / 20 °C / 760 Torr