Multi-step reaction with 11 steps
1: oxalyl chloride, DMF / benzene / Ambient temperature
2: benzene; diethyl ether / -10 - -5 °C
3: Rh(OAc)2 / 1 h / Ambient temperature
4: CeCl3*5H2O, NaBH4 / propan-2-ol; H2O
5: pyridine / 0 °C
6: imidazole / dimethylformamide / Ambient temperature
7: 98 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
8: 46 percent / 80percent AcOH / 48 h / Ambient temperature
9: 96 percent / CBr4, bis(1,2-diphenylphosphino)ethane (DIPHOS) / CH2Cl2 / 0.5 h / Ambient temperature
10: 1.) CuI, n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) from -78 to 0 deg C, 1 h, b) RT, 1 h
11: 61 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
With
rhodium(II) acetate; pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; cerium(III) chloride; oxalyl dichloride; carbon tetrabromide; hydrogen; acetic acid; N,N-dimethyl-formamide; 1,2-bis-(diphenylphosphino)ethane;
Lindlar's catalyst;
In
diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; benzene;
DOI:10.1021/jo00356a004