Multi-step reaction with 10 steps
1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 3.5 h / 20 °C / Inert atmosphere
2: diethyl ether / 4 h / -78 °C / Inert atmosphere
3: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Reflux; Inert atmosphere
4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C / 760.05 Torr / Inert atmosphere
5: dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / toluene / 8 h / -78 - 20 °C / Inert atmosphere
6: water; tin(ll) chloride / ethanol / 2 h / 20 °C / Inert atmosphere
7: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide / dichloromethane; water / 0.5 h / 0 °C / Inert atmosphere
8: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 0 - 20 °C / Inert atmosphere
9: diethylamine / acetonitrile / 20 °C / Inert atmosphere
10: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
With
2,6-dimethylpyridine; dmap; sodium hypochlorite; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; Hoveyda-Grubbs catalyst second generation; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,4,6-trichlorobenzoyl chloride; palladium 10% on activated carbon; water; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; N-ethyl-N,N-diisopropylamine; tin(ll) chloride; potassium bromide;
In
1,4-dioxane; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo1017487