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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
Further Information
Received
29 July 2008
Publication Date:
06 November 2008 (online)
Publication History
Publication Date:
06 November 2008 (online)

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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