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Synthesis 2012(5): 783-787
DOI: 10.1055/s-0031-1289703
DOI: 10.1055/s-0031-1289703
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Total Synthesis of (-)-Pyrenophorol
Further Information
Received
8 October 2011
Publication Date:
13 February 2012 (online)
Publication History
Publication Date:
13 February 2012 (online)

Abstract
An efficient synthetic route has been developed for the synthesis of (-)-pyrenophorol employing Sharpless asymmetric epoxidation, olefin cross-metathesis, and intermolecular Mitsunobu cyclization.
Key words
macrodiolide - stereoselectivity - natural products - Sharpless asymmetric epoxidation - cross-metathesis
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