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Synthesis 2010(21): 3627-3630
DOI: 10.1055/s-0030-1258248
DOI: 10.1055/s-0030-1258248
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Facile Synthesis of (-)-6-Acetoxy-5-hexadecanolide by Organocatalytic α-Oxygenation-Allylation-RCM Strategy
Weitere Informationen
Received
9 July 2010
Publikationsdatum:
07. September 2010 (online)
Publikationsverlauf
Publikationsdatum:
07. September 2010 (online)
![](https://www.thieme-connect.de/media/synthesis/201021/lookinside/thumbnails/10.1055-s-0030-1258248-1.jpg)
Abstract
An asymmetric total synthesis of (-)-6-acetoxy-5-hexadecanolide has been accomplished by employing a seven-step sequence. Asymmetric α-benzoyloxylation of dodecanal followed by indium-mediated one-pot allylation produces the anti-1,2-diol. The six-membered lactone ring is constructed by RCM reaction.
Key words
allylation - α-benzoyloxylation - metathesis - organocatalysts - total synthesis
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At this point, the minor diastereomer is separated by column chromatography in 15% yield.