1: 47 percent / Et3N / tetrahydrofuran / 1 h / 20 °C 2: 1.) N-chlorosuccinimide, triethylamine; 2.) DDQ, Et3N / 1.) methylene chloride, 20 deg C, 30 min; 2.) methylene chloride, 20 deg C, 90 min 3: 85 percent / trifluoroacetic acid / 1 h / 20 °C 4: 82 percent / chlorobenzene / 4 h / 131 °C 5: LiOH View Scheme

1: 1.) N-benzyltrimethylammonium hydroxide, O3, O2, 2.) Me2S / 1.) MeOH, 10 min; -78 deg C, 2.) -78 deg C to r.t., overnight 2: 93 percent / NaBH4 / methanol / 0.5 h / -20 °C 3: 92 percent / H2, HCl, H2O / Pd/C / methanol / 1 h View Scheme

1: 47 percent / Et3N / tetrahydrofuran / 1 h / 20 °C 2: 1.) N-chlorosuccinimide, triethylamine; 2.) DDQ, Et3N / 1.) methylene chloride, 20 deg C, 30 min; 2.) methylene chloride, 20 deg C, 90 min 3: 85 percent / trifluoroacetic acid / 1 h / 20 °C 4: 82 percent / chlorobenzene / 4 h / 131 °C View Scheme

1: 65 percent / tributylstannane, AIBN / benzene / 4 h / Heating 2: 71 percent / H2O, NaOH / Ambient temperature View Scheme