Multi-step reaction with 12 steps
1: 1.) LDA / 1.) THF, a) -78 deg C, 10 min, b) 0 deg C, 1 h, 2.) THF, a) -78 deg C, 15 min, b) 0 deg C, 1 h
2: TsOH*H2O / CH2Cl2 / 0.5 h
3: 58 percent / H2 / 5percent Rh/Al / ethanol / 2 h
4: 96 percent / imidazole / dimethylformamide / 1 h / 0 - 20 °C
5: 91 percent / LDA / tetrahydrofuran / 1 h / -78 °C
6: 89 percent / (i-Bu)2AlH / toluene / 2.5 h / -78 °C
7: 1.) n-BuLi / 1.) THF, 0 deg C, 2 h, 2.) THF, from -78 deg C to 0 deg C, 20 min
8: 1.) borane-methyl sulfide complex, 2.) aq. NaOH, 30percent aq. H2O2 / 1.) Et2O, RT, 2.5 h, 2.) Et2O, EtOH, 0 deg C, 1 h
9: 89 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature
10: 1.) n-BuLi / 1.) THF, a) -78 deg C, 10 min, b) 0 deg C, 1 h, 2.) THF, a) -78 deg C, 30 min, b) from -78 deg C to 0 deg C, 35 min
11: pyridine, DMAP / 18 h / Ambient temperature
12: 6percent Na/Hg, MeOH / tetrahydrofuran / 1 h / -20 °C
With
pyridine; 1H-imidazole; methanol; dmap; sodium hydroxide; sodium amalgam; n-butyllithium; dimethylsulfide borane complex; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide;
rhodium on aluminium;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00375a017
