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田泽酸B的首次全合成。

First Total Synthesis of Tanzawaic Acid B.

作者信息

Murata Takatsugu, Tsutsui Hisazumi, Yoshida Takumi, Kubota Hirokazu, Hiraishi Shintaro, Natsukawa Hiyo, Suzuki Yuki, Hiraga Daiki, Mori Takahiro, Maekawa Yutaro, Tateyama Satoru, Toyoyama Kiyotaka, Ito Keiichi, Suzuki Kyohei, Yonekura Keita, Shibata Natsumi, Sato Teruyuki, Tasaki Yasutaka, Inohana Takehiko, Takano Atsuhiro, Egashira Naoki, Honda Masaki, Umezaki Yuma, Shiina Isamu

机构信息

Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.

出版信息

ACS Omega. 2023 Jul 19;8(30):27703-27709. doi: 10.1021/acsomega.3c03634. eCollection 2023 Aug 1.

DOI:10.1021/acsomega.3c03634
PMID:37546667
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10399178/
Abstract

The first total synthesis of (+)-tanzawaic acid B, a natural polyketide bearing a pentadienoic ester and octalin moiety, has been accomplished. The synthetic improvement from previous synthetic conditions facilitated our gram-scale synthesis of the chiral octalin that possesses seven stereogenic centers and that is the core skeleton of almost all of the tanzawaic acid family.

摘要

(+)-檀泽酸B是一种带有戊二烯酸酯和八氢萘部分的天然聚酮化合物,其首次全合成已经完成。相对于之前的合成条件,合成方法的改进使我们能够以克级规模合成具有七个立体中心的手性八氢萘,该八氢萘是几乎所有檀泽酸家族化合物的核心骨架。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/9cb66388d974/ao3c03634_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/5a5189398a0d/ao3c03634_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/150c2de8afb9/ao3c03634_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/f94894b296b0/ao3c03634_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/12c6ed9f04ea/ao3c03634_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/c7a37d4f7e76/ao3c03634_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/9cb66388d974/ao3c03634_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/5a5189398a0d/ao3c03634_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/150c2de8afb9/ao3c03634_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/f94894b296b0/ao3c03634_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/12c6ed9f04ea/ao3c03634_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/c7a37d4f7e76/ao3c03634_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/9cb66388d974/ao3c03634_0007.jpg

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本文引用的文献

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2
Hatsusamides A and B: Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain FKJ-0213.帽子酰胺 A 和 B:一种由深海来源真菌菌株 FKJ-0213 产生的两种新代谢产物。
Mar Drugs. 2020 Oct 12;18(10):513. doi: 10.3390/md18100513.
3
Tanzawaic acid derivatives from freshwater sediment-derived fungus Penicillium sp.淡水沉积物来源真菌青霉属中分离得到的坦扎瓦酸衍生物
Fitoterapia. 2018 Jul;128:258-264. doi: 10.1016/j.fitote.2018.05.019. Epub 2018 May 17.
4
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J Antibiot (Tokyo). 2018 Jul;71(7):626-632. doi: 10.1038/s41429-018-0049-8. Epub 2018 May 1.
5
Lipid-Lowering Polyketides from the Fungus Penicillium Steckii HDN13-279.从青霉菌 HDN13-279 中提取的降脂多酮。
Mar Drugs. 2018 Jan 12;16(1):25. doi: 10.3390/md16010025.
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Tanzawaic acids isolated from a marine-derived fungus of the genus Penicillium with cytotoxic activities.从具有细胞毒性活性的海洋来源青霉属真菌中分离出的田泽酸。
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Tanzawaic acid derivatives from a marine isolate of Penicillium sp. (SF-6013) with anti-inflammatory and PTP1B inhibitory activities.从海洋青霉菌株(SF-6013)分离得到的具有抗炎和蛋白酪氨酸磷酸酶1B抑制活性的田泽酸衍生物。
Bioorg Med Chem Lett. 2014 Dec 15;24(24):5787-5791. doi: 10.1016/j.bmcl.2014.10.035. Epub 2014 Oct 17.
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