Total synthesis of perylene quinone mycotoxins

苝醌霉菌毒素的全合成

基本信息

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

项目摘要

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.

食品和饲料受霉菌感染会导致农作物损失，并因真菌毒素（霉菌毒素）而导致严重的健康问题。链格孢属代谢物是一类较少被研究的毒素。尤其重要的是间苯二酚内酯和苝醌。尽管一些苝醌毒素具有剧毒，但几乎没有一种毒素被彻底研究过，它们的结构并非全部明确，也没有全合成方法可以为生物学研究提供足够量的毒素。在该提案中，我们描述了全合成，这将产生几种苝醌毒素。具有联苯亚结构的毒素应可从萘-1,5-二醇或联苯-α,α'-二甲醛获得，而具有二氢蒽亚结构的毒素可从四氢萘-1,5-二醇开始获得。关键反应尤其是烯化、亲电芳族酰化和Meinwald重排。进一步的转化将是环氧化、环氧化物开环、二羟基化和羰基化合物的α,β-脱水，具体取决于各自的目标毒素。

项目成果

期刊论文数量（3）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

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