1: 1.) NaH / 1.) benzene, 25 deg C, 1 h, 2.) benzene, 0 deg C 2: 81 percent / aluminum hydride / tetrahydrofuran / 1.5 h / 0 °C 3: 100 percent / CBr4, PPh3 / CH2Cl2 / 1 h / 0 °C 4: 56 percent / acetonitrile / 6 h / 0 °C 5: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2a.) THF, hexane, -78 deg C, 40 min, 2b.) -20 deg C, 30 min 6: 48 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 25 °C 7: 68 percent / K2CO3 / methanol; H2O / 12 h / Ambient temperature View Scheme

Multi-step reaction with 6 steps 1: 87 percent / pyridine, DMAP / 25 °C2: H2O / 120 h / 25 °C / bacteria 4-10T (Klebsiella pneumoniae)3: 96 percent / H2, quinoline / Lindlar catalyst / ethanol / 0.67 h / 760 Torr4: 96 percent / imidazole / tetrahydrofuran / 8 h / 25 °C5: 78 percent / trimethylsilyl iodide, propene / CHCl3 / 0.5 h / 25 °C6: 90 percent / benzene / 16 h / Heating  

Multi-step reaction with 2 steps 1: 55 percent / lead tetraacetate / benzene / 1 h / Ambient temperature2: 61 percent / benzene / 6 h / Heating