1: 78 percent / Cs2CO3 2: 91 percent / DIBAL 3: 74 percent / (COCl)2, DMSO, Et3N 4: 99 percent / Ti(IV) complex with (S)-(-)-binaphthyl amino alcohol 5: 100 percent / LiOH / methanol; H2O View Scheme

Multistep reaction;

Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1: 78 percent / Cs2CO3 2: 91 percent / DIBAL 3: 74 percent / (COCl)2, DMSO, Et3N 4: 95 percent / Ti(IV) complex with (R)-(-)-binaphthyl amino alcohol 5: 100 percent / LiOH / methanol; H2O 6: 98 percent / (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, DIEA 7: 93 percent / LiOH 8: 62 percent / DIAD, PPh3, TsOH*H2O / tetrahydrofuran / 2 h / 0 °C 9: 84 percent / I2 / methanol; H2O View Scheme

palladium diacetate; palladium on activated charcoal; hydrogen 1.) 18 h.; Yield given. Multistep reaction;

2,5-Dihydrothiophene-1,1-dioxide; bis(acetylacetonato) palladium; triethylaluminum; triphenylphosphine in toluene

1: 13 percent / NBS / H2O / 4 h / Ambient temperature 2: 41 percent / conc. methanolic HCl / 2.25 h / Irradiation 3: 25.2 percent / 1,2-dimethoxy-ethane / 0.5 h / 0 °C View Scheme

bis(acetylacetonate)nickel(II); monoethoxy-diethylaluminum; triphenylphosphine in benzene T=60°C; 24 h;

in benzene T=60°C; 24 h; various Ni catalyts; Product distribution;

Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;