Multi-step reaction with 9 steps
1.1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere; Reflux
2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 24 h / 0 - 20 °C
3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
4.1: ethylmagnesium bromide / tetrahydrofuran / 2.75 h / 0 - 50 °C / Inert atmosphere
4.2: 20 °C / Inert atmosphere
5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / Nitroethane / 1.47 h / -78 °C / Inert atmosphere
6.1: platinum(IV) oxide; hydrogen / ethyl acetate / 3 h / 20 °C
7.1: Amberlyst 15.(R). / dichloromethane / 13 h / 20 °C
8.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere
9.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / -78 - 0 °C / Inert atmosphere
9.2: 0.5 h / -78 °C / Inert atmosphere
With
dmap; platinum(IV) oxide; lithium hydroxide monohydrate; boron trifluoride diethyl etherate; ethylmagnesium bromide; hydrogen; diisobutylaluminium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole;
In
tetrahydrofuran; Nitroethane; dichloromethane; water; ethyl acetate; acetone; toluene;
DOI:10.1021/jo201988m