Asymmetric Alkylation of Anthrones, Enantioselective Total Synthesis of (−)- and (+)-Viridicatumtoxins B and Analogues Thereof: Absolute Configuration and Potent Antibacterial Agents
| العنوان: | Asymmetric Alkylation of Anthrones, Enantioselective Total Synthesis of (−)- and (+)-Viridicatumtoxins B and Analogues Thereof: Absolute Configuration and Potent Antibacterial Agents |
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| المؤلفون: | Megan D. McCurry, Yousif Shamoo, Kyriacos C. Nicolaou, Guodu Liu, Kathryn Beabout |
| المصدر: | Journal of the American Chemical Society. 139:3736-3746 |
| بيانات النشر: | American Chemical Society (ACS), 2017. |
| سنة النشر: | 2017 |
| مصطلحات موضوعية: | Models, Molecular, Allylic rearrangement, Alkylation, Stereochemistry, Crystallography, X-Ray, 010402 general chemistry, 01 natural sciences, Biochemistry, Article, Catalysis, chemistry.chemical_compound, Colloid and Surface Chemistry, Viridicatumtoxin B, Anthracenes, Molecular Structure, 010405 organic chemistry, Absolute configuration, Enantioselective synthesis, Total synthesis, Stereoisomerism, General Chemistry, Anti-Bacterial Agents, 0104 chemical sciences, Enantiopure drug, chemistry, Tetracyclines, Organic synthesis |
| الوصف: | A phase transfer catalyzed asymmetric alkylation of anthrones with cyclic allylic bromides using quinidine- or quinine-derived catalysts is described. Utilizing mild basic conditions and as low as 0.5 mol % catalyst loading, and achieving up to >99:1 dr selectivity, this asymmetric reaction was successfully applied to produce enantioselectively (−)- and (+)-viridicatumtoxins B, and thus allowed assignment of the absolute configuration of this naturally occurring antibiotic. While the developed asymmetric synthesis of C10 substituted anthrones is anticipated to find wider applications in organic synthesis, its immediate application to the construction of a variety of designed enantiopure analogues of viridicatumtoxin B led to the discovery of highly potent, yet simpler analogues of the molecule. These studies are expected to facilitate drug discovery and development efforts toward new antibacterial agents. |
| تدمد: | 1520-5126 0002-7863 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::304b5965fddaf4fe4acd96ebd59ef75f https://doi.org/10.1021/jacs.6b12654 |
| حقوق: | OPEN |
| رقم الأكسشن: | edsair.doi.dedup.....304b5965fddaf4fe4acd96ebd59ef75f |
| قاعدة البيانات: | OpenAIRE |
Find this issue from the American Chemical Society | تدمد: | 15205126 00027863 |
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