1: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 2: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C View Scheme

1: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 2: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 3: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h View Scheme

1: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 2: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 3: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 4: 80 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 1 h / 25 °C View Scheme

1: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 2: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 3: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 4: 1.) t-BuLi, 2.) CH3OH / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, - 85 deg C View Scheme

n-butyllithium 1.) ether, hexane, -70 deg C, 10 min, 2.) -55 to -70 deg C, 15 min;; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1: 45 percent / n-buthyl lithium / diethyl ether; hexane; tetrahydrofuran / 0.5 h / -70 °C 2: 1.) acetic acid, 2.) HBr / 1.) 100 deg C, 2.) 0.5 h 3: 98 percent / t-butyl lithium / toluene; diethyl ether; pentane / 1 h View Scheme

1: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 2: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 3: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 4: 1.) t-BuLi / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, from -100 deg C to 0 deg C 5: 49.5percent KHSO5 / tetrahydrofuran; methanol; H2O / 1 h / 30 °C View Scheme

n-butyllithium 1.) ether, hexane, -70 deg C, 10 min, 2.) -55 to -70 deg C, 15 min;; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;