Multi-step reaction with 10 steps
1.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C
2.1: 2.59 g / 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C
3.1: 91 percent / HMPA; n-BuLi / tetrahydrofuran; hexane / 0.67 h / -100 °C
4.1: 98 percent / TsOH*H2O / methanol / 2 h / 20 °C
5.1: 97 percent / MgBr2*Et2O / CH2Cl2 / 1 h / 20 °C
6.1: 83 percent / DBU / CH2Cl2 / 1 h / 0 °C
7.1: H2 / 20 percent Pd(OH)2/C / ethyl acetate / 1 h
8.1: 1.26 g / imidazole / dimethylformamide / 3 h / 20 °C
9.1: BF3*OEt2; molecular sieves 3 Angstroem / CH2Cl2; hexane / 0.33 h / -78 °C
9.2: 72 percent / PPTS / methanol / 4 h / 20 °C
10.1: 95 percent / tetrahydrofuran; toluene / 0.58 h / 0 °C
With
1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 3 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide;
palladium dihydroxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(02)00038-8