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天然癸内酯贝利地辛C和松果毒素的立体选择性全合成

Stereoselective Total Synthesis of Natural Decanolides Bellidisin C and Pinolidoxin.

作者信息

Bi Jingjing, Chen Minhao, Nie Pengpeng, Liu Yuanfang, Liu Jun, Du Yuguo

机构信息

School of Pharmacy, Xinyang Agriculture and Forestry University, Xinyang 464000, China.

School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China.

出版信息

Molecules. 2024 Nov 21;29(23):5500. doi: 10.3390/molecules29235500.

DOI:10.3390/molecules29235500
PMID:39683661
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11643441/
Abstract

A divergent total synthesis of bioactive, naturally occurring decanolides, pinolidoxin and bellidisin C, was accomplished by taking advantage of chiral templates -ribose and -malic acid. In particular, bellidisin C, which is the first total synthesis so far, was achieved through a cascade reaction of reductive elimination and nucleophilic addition in a one-pot process and a sodium-alkoxide-promoted intramolecular lactonization as the key steps.

摘要

通过利用手性模板——核糖和苹果酸,完成了具有生物活性的天然癸内酯、松果毒素和美丽马醉木苷C的发散式全合成。特别是,美丽马醉木苷C的全合成是首次实现,它通过一锅法中还原消除和亲核加成的串联反应以及钠醇盐促进的分子内内酯化作为关键步骤来完成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3c7/11643441/8364515ebe28/molecules-29-05500-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3c7/11643441/86821b46d3b4/molecules-29-05500-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3c7/11643441/645ad70aebcd/molecules-29-05500-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3c7/11643441/74a8e8e72721/molecules-29-05500-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3c7/11643441/8364515ebe28/molecules-29-05500-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3c7/11643441/86821b46d3b4/molecules-29-05500-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3c7/11643441/645ad70aebcd/molecules-29-05500-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3c7/11643441/74a8e8e72721/molecules-29-05500-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3c7/11643441/8364515ebe28/molecules-29-05500-sch003.jpg

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本文引用的文献

1
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J Nat Prod. 2024 Oct 25;87(10):2393-2397. doi: 10.1021/acs.jnatprod.4c00640. Epub 2024 Oct 4.
2
Bioinspired synthesis and biological evaluation of -protulactones A and B.受生物启发的β-原荷叶酮 A 和 B 的合成与生物学评价。
Org Biomol Chem. 2023 Dec 20;22(1):175-183. doi: 10.1039/d3ob01708g.
3
Natural ten-membered lactones: sources, structural diversity, biological activity, and intriguing future.
天然十员环内酯:来源、结构多样性、生物活性及诱人的未来。
Nat Prod Rep. 2024 Jan 24;41(1):85-112. doi: 10.1039/d3np00013c.
4
Stereoselective Total Synthesis of Siladenoserinols A and D.立体选择性全合成西拉登瑟林醇 A 和 D。
Org Lett. 2021 May 7;23(9):3264-3268. doi: 10.1021/acs.orglett.1c00720. Epub 2021 Apr 9.
5
Nonanolides of natural origin: structure, synthesis, and biological activity.天然来源的壬内酯:结构、合成与生物活性。
Curr Med Chem. 2012;19(20):3417-55. doi: 10.2174/092986712801215874.
6
Pinolide, a new nonenolide produced by Didymella pinodes , the causal agent of ascochyta blight on Pisum sativum.豌豆壳球腔菌(Didymella pinodes)产生的新非烯醇内酯类化合物 Pinolide,该菌可引起豌豆壳球腔菌叶斑病。
J Agric Food Chem. 2012 May 30;60(21):5273-8. doi: 10.1021/jf300824d. Epub 2012 May 18.
7
The total synthesis and structural revision of stagonolide D.stagonolide D 的全合成与结构修正。
J Org Chem. 2012 Mar 2;77(5):2169-75. doi: 10.1021/jo202138g. Epub 2012 Feb 15.
8
Bioactive nonanolide derivatives isolated from the endophytic fungus Cytospora sp.从内生真菌 Cytospora sp. 中分离得到的生物活性非诺内酯衍生物
J Org Chem. 2011 Dec 2;76(23):9699-710. doi: 10.1021/jo201755v. Epub 2011 Nov 4.
9
Synthesis of the purported ent-pochonin J structure featuring a stereoselective oxocarbenium allylation.据称的 ent-pochonin J 结构的立体选择性氧杂碳烯烯丙基化合成。
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10
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Org Lett. 2009 Feb 19;11(4):871-4. doi: 10.1021/ol802852r.