1: 1.) NaOMe, 2.) CuCl / 1.) MeOH,benzene, 2.) pyridine, reflux, 20 h 2: 46 percent / Pd(OAc)2 / trifluoroacetic acid; acetic acid / 2.3 h / Heating 3: 17 percent / 1.) n-BuLi, 2.) lithium salt of t-butylperoxide / 1.) n-hexane, Et2O, 4 deg C, 48 h, 2.) -78 deg C -> RT, then reflux, 5 min View Scheme

1: 46 percent / Pd(OAc)2 / trifluoroacetic acid; acetic acid / 2.3 h / Heating 2: 17 percent / 1.) n-BuLi, 2.) lithium salt of t-butylperoxide / 1.) n-hexane, Et2O, 4 deg C, 48 h, 2.) -78 deg C -> RT, then reflux, 5 min View Scheme

1: 1.) NaOMe, 2.) CuCl / 1.) MeOH,benzene, 2.) pyridine, reflux, 20 h 2: 46 percent / Pd(OAc)2 / trifluoroacetic acid; acetic acid / 2.3 h / Heating 3: 17 percent / 1.) n-BuLi, 2.) lithium salt of t-butylperoxide / 1.) n-hexane, Et2O, 4 deg C, 48 h, 2.) -78 deg C -> RT, then reflux, 5 min View Scheme

n-butyllithium; tBuOOLi 1.) n-hexane, Et2O, 4 deg C, 48 h, 2.) -78 deg C -> RT, then reflux, 5 min;