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受生物启发合成来自天然贝壳杉烯酸的 platensimycin。

Bioinspired Synthesis of Platensimycin from Natural -Kaurenoic Acids.

机构信息

Department of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, Spain.

Department of Chemistry, Faculty of Sciences, University of Los Andes, Merida 5101, Venezuela.

出版信息

Org Lett. 2023 Jul 28;25(29):5401-5405. doi: 10.1021/acs.orglett.3c01470. Epub 2023 Jun 20.

Abstract

The biomimetic formal synthesis of the antibiotic platensimycin for the treatment of infection by multidrug-resistant bacteria was accomplished starting from either -kaurenoic acid or grandiflorenic acid, each of which is a natural compound available in multigram scale from its natural source. Apart from the natural origin of the selected precursors, the keys of the described approach are the long-distance functionalization of -kaurenoic acid at C11 and the efficient protocol for the A-ring degradation of the diterpene framework.

摘要

为了治疗多重耐药菌感染,我们从天然来源的 - 贝壳杉烯酸或大柱香叶烯酸这两种天然化合物开始,进行了抗生素 platensimycin 的仿生形式合成。除了所选前体的天然来源外,该方法的关键在于 - 贝壳杉烯酸在 C11 处的远程官能化,以及二萜骨架 A 环降解的有效方案。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ef63/10391625/6a944ceaad0b/ol3c01470_0001.jpg

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