In the Mists of a Fungal Metabolite: An Unexpected Reaction of 2,4,5-Trimethoxyphenylglyoxylic Acid

Immo Serbian; Anne Loesche; Sven Sommerwerk; Phil Liebing; Dieter Ströhl; René Csuk

doi:10.3390/molecules25081978

Molecules (Apr 2020)

In the Mists of a Fungal Metabolite: An Unexpected Reaction of 2,4,5-Trimethoxyphenylglyoxylic Acid

Immo Serbian,
Anne Loesche,
Sven Sommerwerk,
Phil Liebing,
Dieter Ströhl,
René Csuk

Affiliations

Immo Serbian: Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany
Anne Loesche: Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany
Sven Sommerwerk: Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany
Phil Liebing: Otto von Guericke Universität Magdeburg, Chemisches Institut, Universitätsplatz 2, D-39106 Magdeburg, Germany
Dieter Ströhl: Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany
René Csuk: Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany

DOI: https://doi.org/10.3390/molecules25081978
Journal volume & issue: Vol. 25, no. 8
p. 1978

Abstract

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The reactions of phenylglyoxylic acids during the synthesis and biological evaluation of fungal metabolites led to the discovery of hitherto unknown compounds with a p-quinone methide (p-QM) structure. The formation of these p-QMs using 13C-labelled starting materials revealed a key-step of this reaction being a retro-Friedel–Crafts alkylation.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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