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特窗酸的环内过氧化反应

Annulative endoperoxidation of tetronates.

作者信息

Rahimi Najmeh, Sehrish Saba, Akompong Samuel K, Barnes Bayler G, Windorff Cory J, Talipov Marat R, Tello-Aburto Rodolfo

机构信息

Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM, USA.

出版信息

Org Biomol Chem. 2025 Aug 27;23(34):7719-7723. doi: 10.1039/d5ob00663e.

DOI:10.1039/d5ob00663e
PMID:40813344
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12407491/
Abstract

A novel, annulative endoperoxidation of tetronate derivatives bearing unsaturated side chains is presented. The reaction requires a simple setup and proceeds under mild conditions to generate tricyclic endoperoxides in modest diastereoselectivities and useful yields. A free-radical mechanism is proposed.

摘要

本文报道了一种新型的、带有不饱和侧链的特窗酸衍生物的环化内过氧化物反应。该反应装置简单,在温和条件下进行,以适度的非对映选择性和良好的产率生成三环内过氧化物。提出了一种自由基机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/62d0e1245a08/d5ob00663e-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/8186fb5083e1/d5ob00663e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/a3df737b937b/d5ob00663e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/acba3768c5d2/d5ob00663e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/003c3bf126e8/d5ob00663e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/f4daca2d3da0/d5ob00663e-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/62d0e1245a08/d5ob00663e-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/8186fb5083e1/d5ob00663e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/a3df737b937b/d5ob00663e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/acba3768c5d2/d5ob00663e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/003c3bf126e8/d5ob00663e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/f4daca2d3da0/d5ob00663e-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/12536256/62d0e1245a08/d5ob00663e-s5.jpg

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本文引用的文献

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Chem Biodivers. 2024 Oct;21(10):e202400794. doi: 10.1002/cbdv.202400794. Epub 2024 Sep 9.
2
Natural endoperoxides as promising anti-leishmanials.天然内过氧化物有望成为抗利什曼原虫药物。
Phytomedicine. 2024 Jul;129:155640. doi: 10.1016/j.phymed.2024.155640. Epub 2024 Apr 16.
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Catalytic Desymmetrizing Baeyer-Villiger Oxidation of Quaternary Carbon-Containing Cyclobutane-1,3-diones.含季碳的环丁烷-1,3-二酮的催化去对称化拜耳-维利格氧化反应
Org Lett. 2023 Aug 11;25(31):5719-5723. doi: 10.1021/acs.orglett.3c01852. Epub 2023 Jul 28.
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Spin-Forbidden Addition of Molecular Oxygen to Stable Enol Intermediates-Decarboxylation of 2-Methyl-1-tetralone-2-carboxylic Acid.自旋禁阻的分子氧加成到稳定烯醇中间体-2-甲基-1-四氢萘-2-羧酸的脱羧。
Int J Mol Sci. 2023 Apr 18;24(8):7424. doi: 10.3390/ijms24087424.
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The Diverse Modes of Oxygen Reactivity in Life & Chemistry.生命与化学中的多样氧反应模式。
ChemSusChem. 2022 Dec 20;15(24):e202201323. doi: 10.1002/cssc.202201323. Epub 2022 Nov 15.
6
Marine Terpenic Endoperoxides.海洋萜烯内过氧化物。
Mar Drugs. 2021 Nov 25;19(12):661. doi: 10.3390/md19120661.
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Recent advances in the synthesis of naturally occurring tetronic acids.天然四氢呋喃酸的合成研究进展。
Bioorg Chem. 2022 Feb;119:105552. doi: 10.1016/j.bioorg.2021.105552. Epub 2021 Dec 13.
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Artemisinin inspired synthetic endoperoxide drug candidates: Design, synthesis, and mechanism of action studies.受青蒿素启发的合成内过氧化物候选药物:设计、合成及作用机制研究
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Oxidative Ring Expansion of Cyclobutanols: Access to Functionalized 1,2-Dioxanes.环氧化环丁醇:构建功能化 1,2-二氧杂环己烷。
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