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Synthesis 2011(8): 1279-1282
DOI: 10.1055/s-0030-1258458
DOI: 10.1055/s-0030-1258458
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Concise Stereoselective Total Synthesis of Synargentolide A from 3,4,6-Tri-O-acetyl-d-glucal
Further Information
Received
31 December 2010
Publication Date:
03 March 2011 (online)
Publication History
Publication Date:
03 March 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201108/lookinside/thumbnails/10.1055-s-0030-1258458-1.jpg)
Abstract
A short and highly stereoselective synthesis of the naturally occurring, α,β-unsaturated lactone synargentolide A is described from the chiral starting material 3,4,6-tri-O-acetyl-d-glucal. Key steps of the synthesis are lactol opening, Brown’s asymmetric allylation, and a ring-closing metathesis (RCM) reaction.
Key words
3,4,6-tri-O-acetyl-d-glucal - δ-lactones - synargentolide - Brown’s allylation - RCM
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References
Visiting Professor, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.