A diastereoselective synthesis of 7α-nitromethyl steroid derivative and its use for an efficient synthesis of eplerenone

A novel and efficient method of stereoselectively introducing α-nitromethyl group to C-7 position of 11α-hydroxyl canrenone 4 was described. In addition, this method was successfully applied in a total synthesis of Eplerenone 8. The route was characteristic of simple operation, moderate reaction conditions with 5 steps and 55% total yield, at the same time, without any expensive or toxic reagent in use.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A novel and efficient method for stereoselective introduction of nitromethyl group to C-7 position of 11α-hydroxyl canrenone 4. ► A novel total synthesis of eplerenone with five steps and 55% total yield. ► 7α-nitromethyl steroid derivative was afforded for the first time.