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Synthesis 2010(6): 1039-1045
DOI: 10.1055/s-0029-1218638
DOI: 10.1055/s-0029-1218638
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
The Stereoselective Total Synthesis of (+)-Stagonolide B
Weitere Informationen
Received
9 November 2009
Publikationsdatum:
08. Januar 2010 (online)
Publikationsverlauf
Publikationsdatum:
08. Januar 2010 (online)
Abstract
The stereoselective total synthesis of the nonenolide, (+)-stagonolide B is described. The key steps involve epoxide homologation, hydrolytic kinetic resolution and ring-closing metathesis.
Key words
macrolide - ring-closing metathesis - antifungal - phytotoxic - kinetic resolution
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References
The primary alcohol was protected as a TBS-ether and the secondary alcohol was converted into a tosylate. Exposure of the tosylate to 3 equiv of TBAF gave the desired epoxide.