Multi-step reaction with 9 steps
1: 96 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / 20 °C
2: 99 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-dimethylaminopyridine / CH2Cl2 / 0 - 20 °C
3: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C
4: 6.14 g / DMAP / toluene / 1 h
5: 85 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 120 h / 20 °C
6: 95 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
7: 65 percent / Cl2Ru(=CHC6H5)(PCy3)(1,3-Mes2-imidazolidin-2-yl) / 1,2-dichloro-ethane / 120 h / 80 °C
8: 99 percent / DDQ / CH2Cl2; H2O / 0.5 h / 20 °C
9: 90 percent / trifluoroacetic acid / CH2Cl2 / 0 - 20 °C
With
dmap; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride; tetrabutyl ammonium fluoride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; toluene;
DOI:10.1021/ol0350689