Multi-step reaction with 10 steps
1.1: 95 percent / imidazole / dimethylformamide / 12 h / 20 °C
2.1: n-BuLi / hexane; tetrahydrofuran / 0.67 h / cooling
2.2: 75 percent / hexane; tetrahydrofuran / 0.33 h / cooling
3.1: 89 percent / AcONa / ethanol / 12 h / 80 °C
4.1: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C
5.1: 89 percent / MnO2 / CH2Cl2 / 24 h / 20 °C
6.1: 92 percent / aq. HCl / methanol / 3 h / 0 °C
7.1: NaH / dimethylformamide / 0.5 h / cooling
7.2: 93 percent / dimethylformamide / 12 h / 20 °C
8.1: 80 percent / AcOH / 12 h / 90 °C
9.1: 85 percent / pyridine / CH2Cl2 / 4 h / cooling
10.1: 83 percent / Et4NCl; PdCl2(PPh3)2 / dimethylformamide / 4 h / 80 °C
With
pyridine; 1H-imidazole; hydrogenchloride; manganese(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; n-butyllithium; tetraethylammonium chloride; tetrabutyl ammonium fluoride; sodium acetate; sodium hydride; acetic acid;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
10.1: Stille coupling;
DOI:10.1248/cpb.53.393