Tetrahedron

Synthesis of the altertoxin III framework

O Geiseler, M Müller, J Podlech

Index: Geiseler, Oliver; Mueller, Monika; Podlech, Joachim Tetrahedron, 2013 , vol. 69, # 18 p. 3683 - 3689

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Citation Number: 8

Abstract

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 ...