Cu-catalyzed hydroxycyclopropanol ring-opening cyclization to tetrahydrofurans and tetrahydropyrans: short total syntheses of hyperiones,Chemical Science

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Cu-catalyzed hydroxycyclopropanol ring-opening cyclization to tetrahydrofurans and tetrahydropyrans: short total syntheses of hyperiones
Chemical Science ( IF 7.6 ) Pub Date : 2020-11-20 , DOI: 10.1039/d0sc05556e
Weida Liang ₁ , Xinpei Cai ₁ , Mingji Dai ₁

Affiliation

Tetrahydrofurans (THFs) and tetrahydropyrans (THPs) are important core scaffolds frequently found in many molecules of medicinal importance. Herein, we report a novel copper-catalyzed hydroxycyclopropanol ring-opening cyclization methodology to synthesize di- or tri-substituted THFs and THPs. In this reaction, a strained C–C bond was cleaved and a new Csp³–O bond was formed to produce the aforementioned O-heterocycles. The new THF synthesis features a broad substrate scope, scalability, and good functional-group tolerability. It enabled us to complete the shortest enantioselective syntheses of hyperiones A and B (3 and 4 steps, respectively), which is significantly shorter than the previously reported two total syntheses (≥10 steps).

中文翻译：

铜催化羟基环丙醇开环环化生成四氢呋喃和四氢吡喃：海波离子的简短全合成

四氢呋喃（THF）和四氢吡喃（THP）是重要的核心支架，常见于许多具有医学重要性的分子中。在此，我们报告了一种新型铜催化羟基环丙醇开环环化方法来合成二取代或三取代的THF和THP。在此反应中，紧张的 C-C 键被断裂，并形成新的 Csp ³ -O 键，产生上述 O-杂环。新的 THF 合成具有广泛的底物范围、可扩展性和良好的官能团耐受性。它使我们能够完成最短的超离子 A 和 B 的对映选择性合成（分别为 3 和 4 步），这明显短于之前报道的两次总合成（≥10 步）。

更新日期：2020-11-27

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