1: 90 percent / CBr4, Ph3P / acetonitrile / 1.5 h / Ambient temperature 2: 1.) Mg / 1.) THF, 2.) THF, 25 deg C, overnight 3: H2, HCl / 10percent Pd/C / ethanol / 504 h 4: CrO3, pyridine / CH2Cl2 / 0.25 h / 25 °C 5: H2SO4 / 25 °C 6: BBr3 / CH2Cl2 / 3 h / -78 °C 7: NH4Cl, Zn / tetrahydrofuran / 4 h / 60 °C 8: p-TsOH / diethyl ether / 2.5 h / 25 °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