Abstract

A chiral auxiliary is employed to obtain, via Nazarov cyclization, a synthetic intermediate crucial to our previously reported synthesis of the tetrapetalone A core. This indane derivative, corresponding to the A and B rings of the tetrapetalone natural product skeleton, is then used to test an endgame strategy for installation of the β-rhodinosyl group on ring B. A palladium-catalyzed decarboxylative coupling is described that effects the exclusive formation of the desired β-glycosidic linkage, and the target rhodinose moiety can be obtained via hydrogenation.

A chiral auxiliary is employed to obtain, via Nazarov cyclization, a synthetic intermediate crucial to our previously reported synthesis of the tetrapetalone A core. This indane derivative, corresponding to the A and B rings of the tetrapetalone natural product skeleton, is then used to test an endgame strategy for installation of the β-rhodinosyl group on ring B. A palladium-catalyzed decarboxylative coupling is described that effects the exclusive formation of the desired β-glycosidic linkage, and the target rhodinose moiety can be obtained via hydrogenation.

中文翻译：

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合成– SYNLETT演讲：四氢吡咯酮A的不对称合成：富含对映体的茚满中间体的制备和最终糖基化的策略

摘要

使用手性助剂通过Nazarov环化获得合成中间体，该中间体对我们先前报道的四足松A核的合成至关重要。然后，将该茚满衍生物（对应于四petalone天然产物骨架的A和B环）用于测试在B环上安装β-Rhodinosyl基团的最终策略。可以通过氢化获得所需β-糖苷键的形成和目标若丹糖部分。

使用手性助剂通过Nazarov环化获得合成中间体，该中间体对我们先前报道的四足松A核的合成至关重要。然后，将该茚满衍生物（对应于四petalone天然产物骨架的A和B环）用于测试在B环上安装β-Rhodinosyl基团的最终策略。可以通过氢化获得所需β-糖苷键的形成和目标若丹糖部分。