| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 2028776 | Steroids | 2011 | 4 Pages |
Abstract
A new and practical method for a stereoselective construction of a steroid 5α,7α-oxymethylene derivative has been developed and successfully applied to the stereoselective synthesis of eplerenone (8). Starting with available 11α-hydroxyl canrenone (1), eplerenone (8) was synthesised in seven steps with a 48% overall yield.
Research highlights▶ A new and practical method for a stereoselective construction of a steroid 5α,7α-oxymethylene derivative is described. ▶ 1,6-Michael addition of 9(11)-canrenone (3) with i-PrOMe2SiCH2MgCl/CuI·2LiCl or i-PrOMe2SiCH2MgCl/CuBr·Me2S catalyzed by BF3·OEt2 provides the desired 7α addition product. ▶ This method is successfully applied to the stereoselective synthesis of Eplerenone (8).
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Authors
Bin Zhang, Hongli Chen, Huijin Feng, Yuanchao Li,