Journal
SYNLETT
Volume 31, Issue 14, Pages 1409-1412Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690876
Keywords
asymmetric synthesis; coreoside D; polyacetylene glycoside; palladium catalysis; coupling reaction; glycosylation
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Funding
- Institute of Science and Technology, Meiji University
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We report the stereoselective synthesis of (3S)- and (3R)-coreoside D. The conjugated diyne in the C1-C14 moiety was synthesized through two types of palladium-catalyzed cross-coupling reaction. The introduction of the glucopyranose was achieved by a glycosylation reaction using an imidate derivative in the presence of a Lewis acid. The asymmetric center at the C3-position was constructed by the chiral-pool method usingd-malic acid. The stereochemistry at the C3-position of the natural product was determined to beRby comparing the [alpha](D)values of the synthetic stereoisomers with that reported for the natural product.
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