Multi-step reaction with 11 steps
1: 62 percent / Pb(OAc)4 / benzene / 22 h / Heating
2: 95 percent / diethyl ether / -78 deg C to r.t.
3: 56 percent / NaIO4, RuO4*H2O / CCl4; H2O; acetonitrile / 360 h / Ambient temperature
4: 98 percent / i-Pr2NH, DMAP / CH2Cl2 / a) 0 deg C, 6 h, b) r.t., 12 h
5: 99 percent / diisobutylaluminum hydride (DIBAL-H) / tetrahydrofuran; toluene / a) -78 deg C, 15 min, b) -78 deg C to r.t.
6: 76 percent / imidazole / CH2Cl2; dimethylformamide / 1 h / Ambient temperature
7: 87 percent / pyridinium dichromate, PPTS / CH2Cl2 / a) 0 deg C, 1 h, b) r.t., 4 h
8: 82 percent / LDA / tetrahydrofuran / 2 h / -78 deg C to r.t.
9: 74 percent / Et3N / (Ph3P)2PdCl2 / dimethylformamide / 1.25 h / 70 - 75 °C
10: 93 percent / quinoline, H2 / Lindlar catalyst / hexane / 0.25 h / Ambient temperature
11: 2,2,4-trimethyl-pentane / 5 h / 100 °C
With
1H-imidazole; quinoline; lead(IV) acetate; dmap; sodium periodate; dipyridinium dichromate; ruthenium tetroxide; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; diisopropylamine; lithium diisopropyl amide;
bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst;
In
tetrahydrofuran; tetrachloromethane; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)91659-9