Total Synthesis of Artapilosine A and Artapilosine B.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-12-10 DOI:10.1021/acs.jnatprod.4c01149

Guangyan Zhang, Beibei Yang, Li Li, Xuan Pan, Zhanzhu Liu

引用次数: 0

Abstract

Artapilosines A and B, isolated from Artabotrys pilosus, demonstrated significant anti-HIV reverse transcriptase activity. In this work, we present the first asymmetric total synthesis of (-)-artapilosine A and of its enantiomer (+)-artapilosine A, achieved in 10 steps with overall yields of 0.9% and 0.7%, respectively, starting from commercially available piperonylic acid. The key step in this synthesis involved a pivotal photocyclization reaction, providing an efficient protocol for constructing the phenanthrene ring system common to many natural products. Additionally, using the same photocyclization strategy, we successfully synthesized artapilosine B in 10 steps with an overall yield of 2.1%.

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从 Artabotrys pilosus 中分离出的 Artapilosine A 和 B 具有显著的抗艾滋病毒逆转录酶活性。在这项工作中，我们首次不对称地全合成了(-)-artapilosine A 及其对映体(+)-artapilosine A，以市场上可买到的胡椒酸为起点，分 10 步完成，总产率分别为 0.9% 和 0.7%。该合成的关键步骤涉及一个关键的光环化反应，为构建许多天然产品常见的菲环系统提供了一个高效的方案。此外，我们还采用相同的光环化策略，通过 10 个步骤成功合成了 Artapilosine B，总产率为 2.1%。

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

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.