1.1: LDA / tetrahydrofuran / -100 °C 1.2: 84 percent / tetrahydrofuran / -100 °C 2.1: 74 percent / TFA / methanol / 0 °C 3.1: 78 percent / KO(t-Bu) / tetrahydrofuran / 0 °C 4.1: 72 percent / K2CO3 / acetonitrile / 0 - 20 °C 5.1: 62 percent / SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / -20 °C 6.1: 75 percent / DMAP / CH2Cl2 / 20 °C 7.1: 95 percent / Cl2Ru(PCy3)2(=CHPh) / CH2Cl2 / 20 °C 8.1: 100 percent / H2 / Pd/C / methanol / 20 °C 9.1: 85 percent / TFA / CH2Cl2 / 0 °C View Scheme

1: 1.) lithium bis(trimethylsilylamide) / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 1 h 2: 99 percent / m-CPBA 3: 99 percent / H2 / Pd(black) / formic acid; ethanol / r.t., 8 h then 75 deg C, 1.5 h 4: 74 percent / 48 percent HBr, phenol / Heating View Scheme

1: -78 - 20 °C 2: CF3CO2H / methanol View Scheme

hydrogenchloride 1.) Et2O, from -78 to 0 degC; 2.) reflux; Yield given. Multistep reaction;

1: 98 percent / i-Pr2NH; BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 2: 95 percent / TFA / methanol / 15 h / 20 °C 3: 91 percent / Et3N / acetonitrile / 15 h / 20 °C 4: sym-collidine; TFAA / acetonitrile / 0.25 h / 0 °C 5: 1N HCl / tetrahydrofuran / 48 h View Scheme

1: 98 percent / i-Pr2NH; BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 2: 95 percent / TFA / methanol / 15 h / 20 °C 3: 91 percent / Et3N / acetonitrile / 15 h / 20 °C 4: sym-collidine; TFAA / acetonitrile / 0.25 h / 0 °C View Scheme

1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 81 percent / tetrahydrofuran; hexane / -78 °C 2.1: 51 percent / activated Raney-nickel / tetrahydrofuran / 2 h 3.1: 80 percent / CsF / tetrahydrofuran View Scheme

1: 98 percent / i-Pr2NH; BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 2: 95 percent / TFA / methanol / 15 h / 20 °C 3: 91 percent / Et3N / acetonitrile / 15 h / 20 °C 4: sym-collidine; TFAA / acetonitrile / 0.25 h / 0 °C View Scheme

1: 89 percent / LiHMDS / tetrahydrofuran / 0.33 h / -78 °C 2: 97 percent / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: 98 percent / i-Pr2NH; BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 2: 95 percent / TFA / methanol / 15 h / 20 °C 3: 91 percent / Et3N / acetonitrile / 15 h / 20 °C 4: sym-collidine; TFAA / acetonitrile / 0.25 h / 0 °C View Scheme