Multi-step reaction with 14 steps
1: 94 percent / pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 18 h
2: 61 percent / LiClO4, MCPBA / diethyl ether / 20 h / 0 °C
3: 1.) CuBr, DMS / 1.) diethyl ether, 0 deg C, 2.) a) diethyl ether, hexane, o deg C, 2 h, b) RT, 3 h
4: 92 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature
5: 99 percent / H2 / 10percent Pd/C / ethanol / 1 h / 760 Torr
6: 4-(dimethylamino)pyridine / CH2Cl2 / 1.5 h / Ambient temperature
7: 84 percent / LiOH / methanol; H2O / 24 h / Ambient temperature
8: 92 percent / 4-(dimethylamino)pyridine, DCC / CH2Cl2 / 4 h / Ambient temperature
9: HFx*pyridine / tetrahydrofuran / 2 h / Ambient temperature
10: 94 percent / pyridinum chlorochromate, celite / CH2Cl2 / 2 h
11: 73 percent / tetrahydrofuran / 0.25 h / -78 - 0 °C
12: 20 percent / CF3CO2Ag, Na2HPO4 / benzene / 1 h / 82 °C
13: 1.) potassium hexamethyldisilazide, hexamethylphosphoramide, 2.) Et3SiCl, Et3N / 1.) THF, -78 deg C, 15 min, 2.) THF, RT, 4 h
14: 1.) Et3N, Cl2PO2Ph, 2.) Et3N / 1.) THF, 0 deg C, 15 min, 2.) THF, 20 min
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; disodium hydrogenphosphate; 2,3-dimercapto-succinic acid; triethylsilyl chloride; Celite; HFx*pyridine; hydrogen; lithium perchlorate; silver trifluoroacetate; potassium hexamethylsilazane; O-phenyl phosphorodichloridate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; pyridinium chlorochromate; copper(I) bromide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; benzene;
DOI:10.1021/jo00355a013