Multi-step reaction with 15 steps
1.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 40 h / 20 °C / Inert atmosphere
2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1.17 h / -78 °C / Inert atmosphere
2.2: 0.5 h / -78 °C / Inert atmosphere
3.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 17 h / 20 °C / Inert atmosphere
4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 4 h / 20 °C / Inert atmosphere; Molecular sieve
5.1: chromium dichloride; nickel dichloride / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
6.1: pyridine; Dess-Martin periodane / dichloromethane / 4.5 h / 20 °C / Inert atmosphere
7.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.5 h / 0 °C / Inert atmosphere
7.2: Inert atmosphere
8.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / N,N,N,N,N,N-hexamethylphosphoric triamide / 24 h / 70 °C / Inert atmosphere
9.1: 2,6-dimethylpyridine / dichloromethane / 2.55 h / -78 - -45 °C / Inert atmosphere
10.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 14 h / 20 °C / Inert atmosphere
11.1: pyridinium p-toluenesulfonate / methanol / 16 h / 35 °C / Inert atmosphere
12.1: 2,6-dimethylpyridine / dichloromethane / 0.37 h / 0 °C / Inert atmosphere
13.1: camphor-10-sulfonic acid / methanol; dichloromethane / 5 h / 0 °C / Inert atmosphere
14.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0.33 h / 20 °C / Inert atmosphere
15.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 3.5 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; chromium dichloride; dmap; sodium tetrahydroborate; osmium(VIII) oxide; tetrapropylammonium perruthennate; cerium(III) chloride heptahydrate; 5%-palladium/activated carbon; camphor-10-sulfonic acid; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; hydrogen; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; Dess-Martin periodane; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; nickel dichloride;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
5.1: Nozaki-Hiyama-Kishi reaction;
DOI:10.1016/j.tet.2011.04.094