Multi-step reaction with 11 steps
1: pyridine / 6 h / Inert atmosphere
2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 19 h / 0 - 25 °C / Inert atmosphere
3: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 12 h / 25 °C / Inert atmosphere
5: hydroquinidein 1,4-phthalazinediyl diether; potassium carbonate; potassium hexacyanoferrate(III); potassium osmate(VI) / water; tert-butyl alcohol / 18 h / 0 °C / Inert atmosphere
6: 1H-imidazole; dmap / dichloromethane / 1 h / 25 °C / Inert atmosphere
7: triethylamine; magnesium dibromide etherate / dichloromethane / 2 h / 25 °C / Inert atmosphere
8: boron trifluoride diethyl etherate / dichloromethane / 1 h / Inert atmosphere
9: iodine; [bis(acetoxy)iodo]benzene / dichloromethane; cyclohexane / 6 h / 0 °C / Inert atmosphere
10: potassium carbonate / methanol; water / 12 h / 25 °C / Inert atmosphere
11: Jones reagent / acetone / 0.33 h / 0 °C / Inert atmosphere
With
pyridine; 1H-imidazole; triethylsilane; dmap; potassium osmate(VI); Jones reagent; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; iodine; potassium carbonate; magnesium dibromide etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1016/j.steroids.2012.10.021