Hydroxymethylation hydroxylation of 1,3-diarylpropene through a catalytic diastereoselective Prins reaction: cyclization logic and access to brazilin core

IF 4.8 3区化学 Q1 CHEMISTRY, MEDICINAL

Natural Products and Bioprospecting Pub Date : 2024-05-14 DOI:10.1007/s13659-024-00450-2

Xin-Ting Hu, Qing-Yan Cheng, Yan-Ping Chen, Kun Li, Cai-Xian Yan, Dashan Li, Li-Dong Shao

引用次数: 0

Abstract

A catalytic diastereoselective Prins reaction for hydroxymethylation and hydroxylation of 1,3-diarylpropene was successfully utilized to prepare various 1,3-dioxanes 7 in 14–88% yields. Take advantage of the synthetic intermediate 7h, the key B/C rings in brazilin core could be constructed by the sequential of Friedel–Crafts/Ullmann-Ma rather than Ullmann-Ma/Friedel–Crafts reactions.

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通过催化非对映选择性 Prins 反应对 1,3-二芳基丙烯进行羟甲基化：环化逻辑和获得巴西苷核。

利用催化非对映选择性 Prins 反应对 1,3-二芳基丙烯进行羟甲基化和羟基化反应，成功制备了各种 1,3-二氧杂环 7，收率为 14-88%。利用合成中间体 7h 的优势，可以通过 Friedel-Crafts/Ullmann-Ma 而不是 Ullmann-Ma/Friedel-Crafts 反应顺序构建巴西苷核中的关键 B/C 环。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Natural Products and Bioprospecting CHEMISTRY, MEDICINAL-

CiteScore

8.30

自引率

2.10%

发文量

审稿时长

13 weeks

期刊介绍： Natural Products and Bioprospecting serves as an international forum for essential research on natural products and focuses on, but is not limited to, the following aspects: Natural products: isolation and structure elucidation Natural products: synthesis Biological evaluation of biologically active natural products Bioorganic and medicinal chemistry Biosynthesis and microbiological transformation Fermentation and plant tissue cultures Bioprospecting of natural products from natural resources All research articles published in this journal have undergone rigorous peer review. In addition to original research articles, Natural Products and Bioprospecting publishes reviews and short communications, aiming to rapidly disseminate the research results of timely interest, and comprehensive reviews of emerging topics in all the areas of natural products. It is also an open access journal, which provides free access to its articles to anyone, anywhere.