Abstract
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 using d-malic acid. The stereochemistry at the C3-position of the natural product was determined to be R by comparing the [α]D values of the synthetic stereoisomers with that reported for the natural product.
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