Abstract

The heterocyclic ring of tetramic acids is found in naturally occurred biologically active products isolated from fungi, bacteria, molds, and sponges. Thus, these molecules have attracted significant attention as synthetic targets, and various synthetic paths have been developed. Over recent years, a growing number of catalytic approaches toward functionalized products have been established in order to overcome the limitations of the conventional methods. The present review describes the strategies for the metal-catalyzed and metal-promoted synthesis and further derivatization of tetramic acids, with emphasis on recent examples from the literature.

Highlights

  • The present review review describes the strategies for the metal-catalyzed metal-promotedsynthesis synthesisand and further describes the strategies for the metal‐catalyzed andand metal‐promoted derivatization of tetramic acids, with emphasis emphasis on on recent recent examples examples from from the the literature

  • Reutericyclin, tenuazonic acid, streptolydigin, and are representative examplesexamples of biologically active natural whereaswhereas the most well-known equisetin are representative of biologically active products, natural products, the most well‐

  • We found that of the N-acetyl-3-acetyl-5-benzylidenetetramic acid inhibits most of the tested bacterial and fungal the cadmium(II) complex of the N‐acetyl‐3‐acetyl‐5‐benzylidenetetramic acid inhibits most of the strains more effectively than the ligand, and it is potent against Cryptococcus neoformans tested bacterial and fungal strains more effectively than the ligand, and it is potent (MIC = 8 μg/mL) [27]

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Summary

Introduction

Natural and andsynthetic syntheticproducts productsincorporating incorporating tetramic nucleus (pyrrolidine‐2,4‐dione) have been identified as potent antibacterial [3,4,5], antifungal [6], antiviral and anticancer agents [8]. [1,2] have been identified as potent antibacterial [6], [7], antiviral [7], and anticancer These molecules exhibit agricultural bioactivities, such as being fungicidal [9,10,11], agents [8]. Tetramic acids are five-membered five‐membered heterocycles containing the β-dicarbonyl β‐dicarbonyl system and, in the They can can be be functionalized functionalized at position 3 and at case of 3‐acyl β,β′‐tricarbonyl system. The conversion in twoincouples of fast‐converting internal tautomers Factors such as as the solvent, substituents, and temperature influence ratio a/b/c/d.

Tautomeric
Methods
Lacey–Dieckmann Cyclization
Lacey’s
From Meldrum’s Acid
From Phosphorus Ylide Ph3 PCCO
Involving
Examples
Preparation of Tetramic
Yamada’s
SmI2‐Mediated Cyclizations
11. Pettus’
12. Pattenden’s
Pd-Catalyzed Oxidative Aminocarbonylation of 2-Ynylamines
Lithium Telluride‐Triggered Synthesis of Tetramic Acids
14. General
ZrCl44‐Catalyzed
CuI‐Catalyzed toward
Pd‐Catalyzed α‐Arylation of Tetramic Acids
Metal‐Catalyzed 3‐Acylation of Tetramic Acids
Rhodium‐Catalyzed
Annulation Reactions
C‐2 O‐silylated
Findings
Conclusions
Full Text
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