Multi-step reaction with 11 steps
1.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere
1.2: Inert atmosphere; Saturated solution
2.1: 2-picoline borane complex; acetic acid / methanol / 0.5 h / 0 - 20 °C / Inert atmosphere
3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 20 °C / Inert atmosphere
5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C / Inert atmosphere
6.1: water; acetic acid / tetrahydrofuran / Inert atmosphere
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 20 °C / Inert atmosphere
9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 20 °C / Inert atmosphere
10.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere
11.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; 2-picoline borane complex; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; dichloromethane;
11.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2011.08.014