Multi-step reaction with 9 steps
1.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 24 h / 0 - 20 °C
2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 3 h / 20 °C
3.1: ethylmagnesium bromide / tetrahydrofuran / 2.75 h / 0 - 50 °C
3.2: 0.03 h / 20 °C
4.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / tetrahydrofuran; Nitroethane / 1.3 h / -78 °C
5.1: platinum(IV) oxide; hydrogen / ethyl acetate / 3 h / 20 °C
6.1: Amberlyst 15.(R). / dichloromethane / 13 h / 20 °C
7.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere
7.2: 3 h / 20 °C / Inert atmosphere
8.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / -78 - 0 °C / Inert atmosphere
8.2: 0.5 h / -78 °C / Inert atmosphere
9.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol; water; ethyl acetate / 4 h / 20 °C
With
hydrogenchloride; dmap; platinum(IV) oxide; lithium hydroxide monohydrate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; ethylmagnesium bromide; water; hydrogen; diisobutylaluminium hydride; 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; methanol; Nitroethane; dichloromethane; water; ethyl acetate; toluene;
DOI:10.1021/ol202265g