Multi-step reaction with 14 steps
1.1: 80.5 percent / n-Bu4N(1+)*I(1-); NaOH / H2O; CH2Cl2 / 0.42 h / 5 °C
2.1: Zn; AcOH / CH2Cl2 / 10 - 20 °C
3.1: Ac2O / CH2Cl2 / 0.17 h / 5 °C
4.1: 63.3 percent / pyridine; phosphopus oxychloride / CH2Cl2 / 1.17 h / 5 °C
5.1: Bu3SnH; AIBN / acetonitrile / 1.5 h / Heating
5.2: 84.6 percent / I2 / acetonitrile / 1 h / 20 °C
6.1: 12.5 g / DIBAL / toluene / 0.83 h / 5 °C
7.1: 85.3 percent / pyridine / 0.5 h
8.1: 78 percent / triethylamine; Pd(PPh3)4; CuI / 2 h / 70 °C
9.1: 94.3 percent / 4-(dimethylamino)pyridine / acetonitrile / 0.25 h / 20 °C
10.1: 97 percent / H2 / Pd on carbon / ethanol / 3.5 h / 20 °C / 760 Torr
11.1: 96.2 percent / K2CO3 / methanol / 1 h / 20 °C
12.1: 92.7 percent / PPh3; DEAD / benzene; toluene / 0.08 h / 20 °C
13.1: 93 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C
14.1: TMSBr / CH2Cl2 / 0.25 h / -70 °C
14.2: 91.9 percent / phosphate buffer / CH2Cl2; tetrahydrofuran / pH 7.0
With
pyridine; dmap; sodium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 2,2'-azobis(isobutyronitrile); trimethylsilyl bromide; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; acetic anhydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; zinc; diethylazodicarboxylate; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; acetonitrile; benzene;
1.1: Wittig olefination / 8.1: Sonogashira coupling / 12.1: Mitsunobu reaction;
DOI:10.1021/ol034445e