Multi-step reaction with 10 steps
1.1: zinc; sodium iodide / ethanol / 2 h / Reflux
2.1: N-ethyl-N,N-diisopropylamine / 2 h / 20 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C
4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 4 h / 20 °C
5.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 0 - 20 °C
6.1: dmap; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 °C
6.2: 12 h / 0 - 20 °C
7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 36 h / Inert atmosphere; Reflux
8.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 - 0 °C / Inert atmosphere
9.1: benzene / 8 h / 80 °C / Inert atmosphere
10.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 0 °C
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol; benzene;
DOI:10.1016/j.tetlet.2013.04.069