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Remarkable Potential of Zerumbone to Generate a Library with Six Natural Product-like Skeletons by Natural Material-Related Diversity-Oriented Synthesis.
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2020-06-11 , DOI: 10.1021/acs.joc.0c00689
Yoshimi Utaka 1 , Gengo Kashiwazaki 1 , Noriko Tsuchida 2 , Miyuki Fukushima 1 , Issei Takahashi 1 , Yasushi Kawai 3 , Takashi Kitayama 1
Affiliation  

Diversity-oriented synthesis (DOS) is an effective strategy for the quick creation of diverse and high three-dimensional compounds from simple starting materials. The selection of a starting material is the key to constructing useful, chemically diverse compound libraries for the development of new drugs. Here, we report a novel, general, and facile strategy for the creation of diverse compounds with high structural diversity from readily available natural products, such as zerumbone, as the synthetic starting material. Zerumbone is the major component of the essential oil from wild ginger, Zingiber zerumbet Smith. It is noteworthy that zerumbone has a powerful latent reactivity, partly because of its three double bonds, two conjugated and one isolated, and a double conjugated carbonyl group in an 11-membered ring structure. In fact, zerumbone has been shown to be a successful example of natural material-related DOS (NMRDOS). We will report that zerumbone can be converted in one chemical step from four zerumbone derivatives into rare and markedly different scaffolds by transannulation.

中文翻译:

Zerumbone通过与天然物质相关的面向多样性的合成生成具有六个类似天然产物骨架的文库的巨大潜力。

面向多样性的合成(DOS)是一种有效的策略,可以从简单的起始材料快速创建多样的高三维化合物。原材料的选择是构建有用的,化学上多样化的化合物库以开发新药的关键。在这里,我们报告了一种新颖,通用且简便的策略,可从易于获得的天然产物(如蛇骨)作为合成起始材料来创建具有高度结构多样性的多样化合物。球姜酮是精油的野生姜,主要成分红球姜史密斯 值得注意的是,蛇骨酮具有强大的潜在反应性,部分是由于其11个环结构中的三个双键,两个共轭和一个孤立以及一个双共轭羰基。实际上,已经证明了um骨酮是天然材料相关DOS(NMRDOS)的成功实例。我们将报告,可以通过化学转化作用,在一个化学步骤中将蛇骨素从四种蛇骨素衍生物转化为稀有且明显不同的支架。
更新日期:2020-07-02
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