Multi-step reaction with 12 steps
1: 83 percent / dicyclohexylcarbodiimide, dimethyl sulfoxide, trifluoroacetic acid, pyridine / benzene / 2 h / Ambient temperature
2: 80 percent / magnesium chloride / tetrahydrofuran; diethyl ether / 1.) reflux 20 min, 2.) -78 deg C, 1.5 h
3: 95 percent / H2, quinoline / 5percent palladium on calcium carbonate / hexane / 1.5 h
4: 1.) potassium hydride, 18-crown-6, 2.) n-butyllithium / 1.) THF, room temperature, 45 min, 2.) THF, hexane, -78 deg C, 1.5 h
5: 74 percent / p-toluenesulfonic acid / dimethylformamide; H2O / 24 h / Heating
6: 90 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 0.67 h / 0 °C
7: 96 percent / silver carbonate on Celite / benzene / 19 h / Heating
8: 87 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C
9: 94 percent / citric acid / 1.5 h / Heating
10: 88 percent / Dess-Martin periodinane / CH2Cl2 / 2.67 h / Ambient temperature
11: 17 percent / LDA / tetrahydrofuran; hexane / 1 h / -78 °C
12: 81 percent / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / Ambient temperature
With
pyridine; quinoline; dmap; n-butyllithium; 18-crown-6 ether; hydrogen; potassium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; silver carbonate; trifluoroacetic acid; citric acid; magnesium chloride; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja972497r
