Multi-step reaction with 12 steps
1.1: Rh/Al2O3; hydrogen; acetic acid / methanol / 16 h / 2844.39 Torr
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -60 °C
2.2: 2 h / 0 °C
3.1: toluene-4-sulfonic acid / toluene / 3 h / Reflux
4.1: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 - -65 °C / Inert atmosphere
5.1: dichloromethane / 0.5 h / 20 °C
6.1: palladium(II) hydroxide; ammonium formate / ethanol / 2 h / Reflux
7.1: triethylamine; dmap / dichloromethane; ethanol / 0 - 20 °C
8.1: toluene-4-sulfonic acid / acetone / 20 °C
9.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - -60 °C
9.2: 4.5 h / -78 - -10 °C
10.1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere
11.1: potassium carbonate; palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / 1,2-dimethoxyethane; water / 0.15 h / 106 °C / Inert atmosphere
12.1: trifluoroacetic acid / dichloromethane / 1 h
With
dmap; 1,1'-bis-(diphenylphosphino)ferrocene; oxalyl dichloride; Rh/Al2O3; hydrogen; ammonium formate; potassium acetate; palladium diacetate; palladium(II) hydroxide; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; acetone; toluene;
2.1: |Swern Oxidation / 11.1: |Suzuki Coupling;
DOI:10.1021/jm3011299