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Synthesis 2008(23): 3801-3804
DOI: 10.1055/s-0028-1087226
DOI: 10.1055/s-0028-1087226
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Nonclassical Stereoselective Semi-Synthesis of Drospirenone via Cross-Metathesis Reaction
Weitere Informationen
Received
29 July 2008
Publikationsdatum:
06. November 2008 (online)
Publikationsverlauf
Publikationsdatum:
06. November 2008 (online)
![](https://www.thieme-connect.de/media/synthesis/200823/lookinside/thumbnails/10.1055-s-0028-1087226-1.jpg)
Abstract
A new synthetic approach for the construction of the spirolactone moiety of the progestin drospirenone is presented. A highly efficient cross-metathesis reaction catalyzed by Grubbs-Hoveyda second-generation catalyst (6 mol%) is employed as the key step for the introduction of the ester moiety on to the vinyl group at C17. No protecting groups are required and harmful heavy-metal-based oxidants are not used and this means that this route constitutes a valuable synthetic alternative to existing approaches.
Key words
cross-metathesis - drospirenone - stereoselection - steroids - synthesis
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