Stereoselective synthesis of β-lactams: recent examples

Saura‐Sanmartin, Adrian; Andreu-Ardil, Laura

doi:10.1039/d3ob00309d

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00309d

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Stereoselective synthesis of β-lactams: recent examples

Adrian Saura‐Sanmartin

Laura Andreu-Ardil

Abstract: The synthesis of β-lactam derivatives is a research topic of great interest due to the biological activity of these molecules. Indeed, there are several antibiotics wich include a β-lactam core...

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2024

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Cited by 3 publications

References 76 publications

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Rapid Access to Chiral Spiro[2.3] Lactams: Stereoselective Hydroborylation and Hydrosilylation and Remote Control of Axial Chirality by Copper-Catalyzed Desymmetrization of Spirocyclopropenes

Zhou,

Liang,

et al. 2024

Org. Lett.

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Chiral spirocyclopropyl β-lactams are common motifs in bioactive compounds and pharmaceuticals. Here we disclose a diastereoselective and enantioselective hydroborylation and hydrosilylation of spirocyclopropenes, via a Cu-catalyzed desymmetrization strategy, for the rapid preparation of enantio-enriched spirocyclopropyl β-lactams. The efficient desymmetrization strategy allows the remote control of axial chirality, offering the borylated and silylated products bearing central, spiro, and axial chirality. The combination of multichiral elements would provide a novel motif for biological evaluation in potential drug discovery.

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Rapid Access to Chiral Spiro[2.3] Lactams: Stereoselective Hydroborylation and Hydrosilylation and Remote Control of Axial Chirality by Copper-Catalyzed Desymmetrization of Spirocyclopropenes

Zhou,

Liang,

et al. 2024

Org. Lett.

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Forging structural complexity: diastereoselective synthesis of densely substituted β-lactams with dual functional handles for enhanced core modifications

Rodriguez Treviño,

Loch-Temzelides,

Pandiri

et al. 2024

Chem. Sci.

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Chemical Methods for the Construction of Spirocyclic β-Lactams and Their Biological Importance

Berry,

Bhalla,

Yadav

2024

Synthesis

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Spirocyclic β-lactams are a family of natural and synthetic chemicals with different biological activity, including antibacterial properties and interaction with critical physiological targets such as T-type calcium channels and acetyl-CoA cholesterol acyltransferase. Their unique chemical structure, combining spiro ring system with β-lactam group, offers promising opportunities for targeted medication discovery in medicinal chemistry. Spirocyclic β-lactams have the potential to be adaptable frameworks for developing novel therapeutic medicines with particular three-dimensional pharmacophoric characteristics and increased biological efficacy. Numerous methods are employed in the synthesis of spirocyclic β-lactams, such as cyclization, functional group modifications, asymmetric synthesis utilizing chiral catalysts and biomimetic approaches. In this Short Review, two distinct approaches to recent synthesis of spirocyclic β-lactams are discussed: one is based on constructing the β-lactam ring, while the other entails transforming monocyclic β-lactams into spirocyclic structures (from 2021 to till date). These methods include detailed reaction processes and biological function descriptions of target spirocycles. The applications of spirocyclic β-lactams in medicinal chemistry highlight their role in synthesis of structurally diverse compounds with significant therapeutic potential, demonstrating creative chemical methods of building complex molecular structures. 1 Introduction 2 β-Lactam Ring Synthesis 3 Non-β-Lactam Ring Synthesis 4 Miscellaneous Examples 5 Conclusion and Outlook 6 References

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Stereoselective synthesis of β-lactams: recent examples

Abstract: The synthesis of β-lactam derivatives is a research topic of great interest due to the biological activity of these molecules. Indeed, there are several antibiotics wich include a β-lactam core...

Cited by 3 publications

References 76 publications

Rapid Access to Chiral Spiro[2.3] Lactams: Stereoselective Hydroborylation and Hydrosilylation and Remote Control of Axial Chirality by Copper-Catalyzed Desymmetrization of Spirocyclopropenes

Rapid Access to Chiral Spiro[2.3] Lactams: Stereoselective Hydroborylation and Hydrosilylation and Remote Control of Axial Chirality by Copper-Catalyzed Desymmetrization of Spirocyclopropenes

Forging structural complexity: diastereoselective synthesis of densely substituted β-lactams with dual functional handles for enhanced core modifications

Chemical Methods for the Construction of Spirocyclic β-Lactams and Their Biological Importance

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