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Divergent Total Syntheses of Yaequinolone-Related Natural Products by Late-Stage C-H Olefination.

ABSTRACT: Divergent total syntheses of 10 yaequinolone-related natural products have been achieved for the first time by late-stage C-H olefination of 3,4-dioxygenated 4-aryl-5-hydroxyquinolin-2(1H)-ones, core structures of this family of natural products. A robust synthetic methodology to construct the core structures has been established, and the C-H olefination reaction has been carried out with synthetically useful yields and high levels of site-selectivity under mild reaction conditions in the presence of a Pd/S,O-ligand catalyst.

SUBMITTER: Jia WL

PROVIDER: S-EPMC8154619 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Divergent Total Syntheses of Yaequinolone-Related Natural Products by Late-Stage C-H Olefination.

Jia Wen-Liang WL Ces Sabela Vega SV Fernández-Ibáñez M Ángeles MÁ

The Journal of organic chemistry 20210422 9

Divergent total syntheses of 10 yaequinolone-related natural products have been achieved for the first time by late-stage C-H olefination of 3,4-dioxygenated 4-aryl-5-hydroxyquinolin-2(1<i>H</i>)-ones, core structures of this family of natural products. A robust synthetic methodology to construct the core structures has been established, and the C-H olefination reaction has been carried out with synthetically useful yields and high levels of site-selectivity under mild reaction conditions in the ...[more]

PMID: 33886329

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