Rapid Access to Tigliane, Ingenane, and Rhamnofolane Diterpenes from a Lathyrane Precursor via Biomimetic Skeleton Transformation Strategy

IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-05-10 DOI:10.1021/acs.jnatprod.4c00364
Neng Wang, Lin-Xi Wan, Xiaohuan Li, Jin-Bu Xu* and Feng Gao*, 
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Abstract

Bioinspired skeleton transformation of a tricyclic lathyrane-type Euphorbia diterpene was conducted to efficiently construct a tetracyclic tigliane diterpene on a gram scale via a key aldol condensation. The tigliane diterpene was then respectively converted into naturally rare ingenane and rhamnofolane diterpenes through a semipinacol rearrangement and a visible-light-promoted regioselective cyclopropane ring-opening reaction. This work provides a concise strategy for high-efficiency access to diverse polycyclic Euphorbia diterpene skeletons from abundant lathyrane-type natural products and paves the way for biological activity investigation of naturally rare molecules.

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通过生物仿生骨架转化策略,从一种 Lathyrane 前体中快速获得 Tigliane、Ingenane 和 Rhamnofolane 二萜。
通过生物启发对一种三环扁桃烯型大戟二萜进行骨架转化,通过关键的醛醇缩合在克级规模上高效地构建了四环惕各烷二萜。然后,通过半频哪醇重排反应和可见光促进的区域选择性环丙烷开环反应,将噻格连二萜分别转化为天然稀有的锭烷和鼠李糖二萜。这项工作提供了一种简明的策略,可从丰富的百里香类天然产物中高效获取多种多环大戟二萜骨架,并为天然稀有分子的生物活性研究铺平了道路。
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来源期刊
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.
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