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通过锍叶立德高效合成稠合多环醚体系:对岩沙海葵毒素和阿德里亚毒素的一种合成方法。

Efficient Synthesis of Fused Polycyclic Ether Systems via Sulfonium Ylides: A Synthetic Approach to Yessotoxin and Adriatoxin.

作者信息

Moya-Utrera Federico, Cheng-Sánchez Iván, Fuentes-Pino Irama, Sánchez-Ruiz Antonio, Sarabia Francisco

机构信息

Department of Organic Chemistry, Faculty of Sciences, University of Málaga, 29071 Málaga, Spain.

Faculty of Pharmacy, University of Castilla-La Mancha, Campus de Albacete, Avda. Dr. José María Sánchez Ibáñez S/N, 02008 Albacete, Spain.

出版信息

Mar Drugs. 2025 Jan 21;23(2):51. doi: 10.3390/md23020051.

DOI:10.3390/md23020051
PMID:39997175
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11857374/
Abstract

A novel class of chiral sulfonium salts, derived from L- and D-methionine, was designed and successfully employed for the diastereoselective synthesis of epoxy amides. This new methodology of asymmetric epoxidation was exploited for the stereoselective construction of fused polycyclic ethers, which are structural motifs present in a great variety of natural products of marine origin. This methodology proved to be useful for the synthesis of the tricyclic system contained in yessotoxin and adriatoxin, and also in many other related natural products of marine origin belonging to the fused polycyclic ether toxins.

摘要

设计了一类新型的源自L-和D-蛋氨酸的手性锍盐,并成功用于环氧酰胺的非对映选择性合成。这种不对称环氧化的新方法被用于立体选择性构建稠合多环醚,稠合多环醚是多种海洋来源天然产物中存在的结构基序。该方法被证明可用于合成岩沙海葵毒素和阿德里亚毒素中所含的三环体系,以及许多其他属于稠合多环醚毒素的海洋来源相关天然产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/e0f5105163e3/marinedrugs-23-00051-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/91ab3f88db93/marinedrugs-23-00051-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/3161d4106f88/marinedrugs-23-00051-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/d6b304f96905/marinedrugs-23-00051-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/a67b459d06e5/marinedrugs-23-00051-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/e2da1e972610/marinedrugs-23-00051-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/89e67110b6c8/marinedrugs-23-00051-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/0ef274da2e25/marinedrugs-23-00051-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/e0f5105163e3/marinedrugs-23-00051-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/91ab3f88db93/marinedrugs-23-00051-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/3161d4106f88/marinedrugs-23-00051-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/d6b304f96905/marinedrugs-23-00051-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/a67b459d06e5/marinedrugs-23-00051-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/e2da1e972610/marinedrugs-23-00051-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/89e67110b6c8/marinedrugs-23-00051-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/0ef274da2e25/marinedrugs-23-00051-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f5f1/11857374/e0f5105163e3/marinedrugs-23-00051-sch007.jpg

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BMC Cardiovasc Disord. 2025 Jan 15;25(1):23. doi: 10.1186/s12872-025-04483-4.
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Continuous Flow Chemistry: A Novel Technology for the Synthesis of Marine Drugs.连续流动化学:一种用于海洋药物合成的新型技术。
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Alzheimer's Disease and Toxins Produced by Marine Dinoflagellates: An Issue to Explore.
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Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products.基于合成策略的海洋多环醚天然产物的立体化学结构确定。
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Structure Elucidation and Relative Toxicity of (24)-24-Hydroxyyessotoxin from a Namibian Isolate of .结构解析与(24)-24-羟基岩沙海葵毒素的相对毒性,来自纳米比亚分离株。
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