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  4. Total Asymmetric Syntheses of beta-Hydroxy-delta-lactones via Umpolung with Sulfur Dioxide
 
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research article

Total Asymmetric Syntheses of beta-Hydroxy-delta-lactones via Umpolung with Sulfur Dioxide

Exner, Claudia J.  
•
Laclef, Sylvain
•
Poli, Florent
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2011
The Journal of Organic Chemistry

Cyclic stereotriads and stereotetrads of the beta-hydroxy-delta-lactone type, e.g. prelactones B and E, common in polyketides and polypropionates, are prepared via SO2-induced oxyallylations of enoxysilanes with (1E,3Z)-1-(1-phenylethoxy)penta-1,3-dien-3-yl carboxylates. Using (Z)- or (E)-enoxysilanes both 4,5-cis- or 4,5-trans-delta-lactones are obtained. Depending on the reduction method applied to the obtained aldol intermediates 5,6-trans or 5,6-cis-derivatives are formed. The delta-lactones can be prepared in both their enantiomeric forms depending on the (1R)- or (1S)-configuration of the starting 1-(1-phenylethoxy)penta-1,3-dienes.

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Type
research article
DOI
10.1021/jo102035d
Web of Science ID

WOS:000286577400011

Author(s)
Exner, Claudia J.  
•
Laclef, Sylvain
•
Poli, Florent
•
Turks, Maris  
•
Vogel, Pierre  
Date Issued

2011

Published in
The Journal of Organic Chemistry
Volume

76

Start page

840

End page

845

Subjects

Modular Polyketide Synthase

•

Precursor-Directed Biosynthesis

•

Ring-Closing Metathesis

•

Marine Natural-Products

•

Enantioselective Synthesis

•

Prelactone-B

•

Erythromycin Biosynthesis

•

Stereoselective-Synthesis

•

Polypropionate Synthesis

•

Antibiotic Kendomycin

Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
December 16, 2011
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/74440
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