Total synthesis of perylene quinone mycotoxins

苝醌霉菌毒素的全合成

• 批准号: 318341891
• 负责人: Professor Dr. Joachim Podlech
• 金额: --
• 依托单位: Institut für Organische Chemie (IOC)
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2016
• 资助国家: 德国
• 起止时间: 2015-12-31 至 2019-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/318341891?language=en
• 关键词: Total; synthesis; perylene; quinone; mycotoxins

Infestation of food and feed with mould fungi leads to crop losses and due the fungal toxins (mycotoxins) to severe health problems. Alternaria metabolites are a less investigated class of toxins; especially important are the resorcylic lactones and the perylene quinones. Though some of the perylene quinone toxins are highly toxic, hardly any of these were thoroughly investigated, not all of their structures are not unambiguously clear, and no total synthesis is available, which could supply sufficient amounts of the toxins for biological investigations. In this proposal we describe total syntheses, which would lead to several perylene quinone toxins. Toxins with a biphenyl substructure should be accessible from either naphthalene-1,5-diol or from biphenyl-alpha,alpha'-dicarbaldehyde and toxins with a dihydroanthracene substructure could be approached starting with tetralin-1,5-diol. Key reactions would be inter alia olefinations, electrophilic aromatic acylations, and Meinwald rearrangements. Further transformation would be epoxidations, opening of epoxides, dihydroxylations, and alpha,beta-dehydrations of carbonyl compounds, depending on the respective target toxin.

霉菌对食物和饲料的侵染导致作物损失，并由于真菌毒素（霉菌毒素）导致严重的健康问题。链格孢属代谢物是研究较少的一类毒素;特别重要的是二羟基苯甲酸内酯和二萘嵌苯醌。虽然一些苝醌毒素是高毒性的，但几乎没有任何一种毒素被彻底研究，并非所有的结构都是明确的，并且没有全合成，这可以为生物学研究提供足够量的毒素。在这个建议中，我们描述了全合成，这将导致几个苝醌毒素。具有联苯子结构的毒素应该可以从萘-1，5-二醇或从联苯-α，α ′-二甲醛获得，而具有二氢蒽子结构的毒素可以从四氢化萘-1，5-二醇开始获得。关键反应阿利亚是烯烃化、亲电芳族酰化和Meinwald重排。进一步的转化将是环氧化、环氧化物的开环、二羟基化和羰基化合物的α，β-脱水，这取决于相应的靶毒素。

项目成果

DNA reactivity of altertoxin II: Identification of two covalent guanine adducts formed under cell-free conditions.

改变毒素 II 的 DNA 反应性：鉴定无细胞条件下形成的两种共价鸟嘌呤加合物

• DOI: 10.1016/j.toxlet.2020.05.018
• 发表时间: 2020
• 期刊: Toxicology letters
• 影响因子: 3.5
• 作者: Sebastian T. Soukup;Stefanie C. Fleck;Erika Pfeiffer;Joachim Podlech;Sabine E. Kulling;Manfred Metzler
• 通讯作者: Manfred Metzler

Synthesis of cis‐ and trans‐Configured Octahydroperylenes

顺式和反式构型八氢苝的合成

• DOI: 10.1002/ejoc.201701218
• 发表时间: 2017
• 期刊: European Journal of Organic Chemistry
• 影响因子: 2.8
• 作者: Dominik Pfaff;Sebastian Bestgen;Joachim Podlech
• 通讯作者: Joachim Podlech