Tetramic acid derivatives via Ugi–Dieckmann-reaction

Spatz, Julia H.; Welsch, Sebastian J.; Duhaut, David-Emmanuel; Jäger, Nadine; Boursier, Thomas; Fredrich, Martin; Allmendinger, Lars; Ross, Günther; Kolb, Juergen F.; Burdack, Christoph; Umkehrer, Michael

doi:10.1016/j.tetlet.2009.01.124

Cited by 25 publications

(10 citation statements)

References 31 publications

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“…The tetramic acid structural moiety is a very important nitrogen-containing heterocycle that is often the pharmacophore to interact with various biological targets, thus it exhibits a wide range of biological and toxicological activities [ 52 , 53 , 54 ]. Apart from α-CPA, 2-oxoCPA and speradine A, for which the SERCA-blocking activity was clearly demonstrated, the toxicological profile for the rest of the CPA-type metabolites is unknown [ 4 , 12 , 34 ].…”

Section: Discussionmentioning

confidence: 99%

Unravelling the Diversity of the Cyclopiazonic Acid Family of Mycotoxins in Aspergillus flavus by UHPLC Triple-TOF HRMS

Uka

Moore

Arroyo‐Manzanares

et al. 2017

Toxins

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Cyclopiazonic acid (α-cyclopiazonic acid, α-CPA) is an indole-hydrindane-tetramic acid neurotoxin produced by various fungal species, including the notorious food and feed contaminant Aspergillus flavus. Despite its discovery in A. flavus cultures approximately 40 years ago, its contribution to the A. flavus mycotoxin burden is consistently minimized by our focus on the more potent carcinogenic aflatoxins also produced by this fungus. Here, we report the screening and identification of several CPA-type alkaloids not previously found in A. flavus cultures. Our identifications of these CPA-type alkaloids are based on a dereplication strategy involving accurate mass high resolution mass spectrometry data and a careful study of the α-CPA fragmentation pattern. In total, 22 CPA-type alkaloids were identified in extracts from the A. flavus strains examined. Of these metabolites, 13 have been previously reported in other fungi, though this is the first report of their existence in A. flavus. Two of our metabolite discoveries, 11,12-dehydro α-CPA and 3-hydroxy-2-oxo CPA, have never been reported for any organism. The conspicuous presence of CPA and its numerous derivatives in A. flavus cultures raises concerns about the long-term and cumulative toxicological effects of these fungal secondary metabolites and their contributions to the entire A. flavus mycotoxin problem.

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Section: Discussionmentioning

confidence: 99%

Unravelling the Diversity of the Cyclopiazonic Acid Family of Mycotoxins in Aspergillus flavus by UHPLC Triple-TOF HRMS

Uka

Moore

Arroyo‐Manzanares

et al. 2017

Toxins

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“…The crude residue was then exposed to a series of different cyclization reaction conditions. First, based on the previous works on the Dieckmann cyclization reaction [40,41], we investigated the effect of different inorganic and organic bases ( Table 1). It was interesting to note that all of the bases tested in the study afforded the desired enol tetramic acid derivative 7a after the reaction was heated under the microwave irradiation conditions.…”

Section: Resultsmentioning

confidence: 99%

“…In recent years, we used the Ugi four-component reaction as a main tool to generate nitrogen-containing heterocycles [38,39]. Spatz' team reported a novel two-step synthetic procedure for the preparation of substituted tetramic acid derivatives via an Ugi/Dieckmann reaction [40]. A leaving amide that was derived from the isonitrile, provided the tetramic acid core under strong inorganic basic conditions.…”

Section: Microwave-assisted Efficient and Facile Synthesis Of Tetramimentioning

confidence: 99%

Microwave-assisted efficient and facile synthesis of tetramic acid derivatives via a one-pot post-Ugi cascade reaction

Li¹,

Huang²,

Xu³

et al. 2020

Beilstein J. Org. Chem.

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A facile microwave-assisted method for the synthesis of tetramic acid derivatives has been developed through an Ugi/Dieckmann cyclization strategy with DBU. This two-step one-pot procedure afforded the targeted tetramic acid analogues in good yields. With commercially available Ugi starting materials, microwave irradiation, a simple operation, excellent yields, and a broad scope, this reaction has the potential to produce a large number of tetramic acid analogues, which cannot be easily accessed by the classic synthetic methods. 663

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“…This present study involved the development of a route based on phenylene triamines (2) that allowed the introduction of diversity into the 2-position of the product benzimidazole ring (3). After introducing a piperazine derivative onto the 3-position of the phenylene triamine, the key diversity step was the creation of 40 benzimidazoles by HATU-catalysed coupling with carboxylic acids, and then cyclisation by brief heating in acetic acid.…”

Section: Parallel Synthesis Of Gonadotrophin Releasing Hormone Antagomentioning

confidence: 99%

Combinatorial Chemistry Online Volume 11, Issue 5, May 2009

Terrett

2009

Combinatorial Chemistry - an Online Journal

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Tetramic acid derivatives via Ugi–Dieckmann-reaction

Cited by 25 publications

References 31 publications

Unravelling the Diversity of the Cyclopiazonic Acid Family of Mycotoxins in Aspergillus flavus by UHPLC Triple-TOF HRMS

Unravelling the Diversity of the Cyclopiazonic Acid Family of Mycotoxins in Aspergillus flavus by UHPLC Triple-TOF HRMS

Microwave-assisted efficient and facile synthesis of tetramic acid derivatives via a one-pot post-Ugi cascade reaction

Combinatorial Chemistry Online Volume 11, Issue 5, May 2009

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