Cu-catalyzed hydroxycyclopropanol ring-opening cyclization to tetrahydrofurans and tetrahydropyrans: short total syntheses of hyperiones. Issue 4 (26th November 2020)

• Record Type: Journal Article
• Authors: Liang, Weida; Cai, Xinpei; Dai, Mingji
• Is Part Of: Chemical science. Volume 12:Issue 4(2021)
• Page Start: 1311
• Page End: 1316
• Publication Date: 2020-11-26
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc05556e
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A novel Cu-catalyzed hydroxycyclopropanol ring-opening cyclization was developed to synthesize substituted tetrahydrofuran/tetrahydropyran molecules including two norlignan natural products hyperiones A and B. Abstract : 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 Csp 3 –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).