Synthesis of C-acyl furanosides via the cross-coupling of glycosyl esters with carboxylic acids.
Synthesis of C-acyl furanosides via the cross-coupling of glycosyl esters with carboxylic acids.
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DOI：
10.1039/d1sc03596g
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发表时间：
2021-09-01
期刊：
影响因子：
8.4
通讯作者：
Diao T
中科院分区：
文献类型：
--
作者：
Wei Y;Lam J;Diao T
C-酰基呋喃糖苷是多种天然产物、核苷类似物和药物分子的多功能合成前体。本报告介绍了在糖酯和羧酸之间的交叉偶联反应制备C-酰基呋喃糖苷方面尚未解决的挑战。关键的一步是糖基酯的光氧化还原活化，它通过放出二氧化碳来促进强异常C-O键的均解，从而提供糖基自由基。该方法涵盖了较大范围的呋喃类、吡喃类和羧酸类化合物，适用于胸苷类似物和双呋喃酮B的合成，以及(+)-Sclareolide的后期修饰。从天然糖中制备氧化还原活性糖酯的简便方法，以及与常见呋喃类化合物的配伍性，体现了该方法在药物化学中的潜力。糖基酯与羧酸的交叉偶联以制备C-酰基呋喃糖苷和吡喃糖苷。该反应通过糖酯的光氧化还原活化来提供糖基自由基。
C-Acyl furanosides are versatile synthetic precursors to a variety of natural products, nucleoside analogues, and pharmaceutical molecules. This report addresses the unmet challenge in preparing C-acyl furanosides by developing a cross-coupling reaction between glycosyl esters and carboxylic acids. A key step is the photoredox activation of the glycosyl ester, which promotes the homolysis of the strong anomeric C–O bond through CO2 evolution to afford glycosyl radicals. This method embraces a large scope of furanoses, pyranoses, and carboxylic acids, and is readily applicable to the synthesis of a thymidine analogue and diplobifuranylone B, as well as the late-stage modification of (+)-sclareolide. The convenient preparation of the redox active glycosyl ester from native sugars and the compatibility with common furanoses exemplifies the potential of this method in medicinal chemistry. A cross-coupling of glycosyl esters with carboxylic acids to prepare C-acyl furanosides and pyranosides. The reaction proceeds through photoredox activation of the glycosyl ester to afford glycosyl radicals.
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