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

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 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).

SUBMITTER: Liang W

PROVIDER: S-EPMC8179039 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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

Liang Weida W Cai Xinpei X Dai Mingji M

Chemical science 20201120 4

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<sup>3</sup>-O bond was formed to produce the aforementioned O-heterocycles. The new THF synthesis features a broad substrate scope, scalabilit ...[more]

PMID: 34163894

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