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.

中文翻译：

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Coreoside D 的立体选择性合成及其绝对构型的测定

我们报告了 (3S)- 和 (3R)-coreoside D 的立体选择性合成。 C1-C14 部分中的共轭二炔是通过两种钯催化的交叉偶联反应合成的。在路易斯酸的存在下，通过使用亚胺酸酯衍生物的糖基化反应来实现吡喃葡萄糖的引入。C3 位的不对称中心是通过手性池方法使用 d-苹果酸构建的。通过比较合成立体异构体的 [α] D 值与天然产物报道的值，确定天然产物 C3 位的立体化学为 R。