Synthesis of the altertoxin III framework
Synthesis of the altertoxin III framework
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DOI：
10.1016/j.tet.2013.03.013
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发表时间：
2013-05-06
期刊：
影响因子：
2.1
通讯作者：
Podlech, Joachim
中科院分区：
文献类型：
--
作者：
Geiseler, Oliver;Mueller, Monika;Podlech, Joachim
本文首次合成了由链格孢属真菌产生的污染食品和饲料的真菌毒素--链格孢毒素III的骨架。包括蒽衍生物的Diels-Alder反应在内的合成方案由于关键中间体的芳构化而不成功。通过DFT计算进一步研究了这种芳构化，结果表明，芳构化趋势取决于所连接取代基的电子特性。一个Friedel-Crafts型铪三氟甲磺酸盐催化二聚二羟基四氢化萘与随后的苄基氧化提供的目标化合物，这应该是一个合适的前体合成altertoxin III和相关的天然产物。(C)2013爱思唯尔有限公司保留所有权利。
The framework of altertoxin III, a mycotoxin produced by Alternaria fungi investing food and feed, has been synthesised for the first time. Synthetic schemes including Diels-Alder reactions of anthracene derivatives turned out to be not successful due to an aromatisation of key intermediates. This aromatisation was further investigated by DFT calculations, which showed that the aromatisation tendency is dependant from the electronic characteristics of attached substituents. A Friedel-Crafts-type hafnium triflate-catalysed dimerisation of dihydroxytetralins with subsequent benzylic oxidation furnished the target compound, which should be a suitable precursor for the synthesis of altertoxin III and related natural products. (C) 2013 Elsevier Ltd. All rights reserved.