Abstract
Because the renewed interest of β – lactams in organic and medicinal chemistry, research in this field continues in producing new appealing progresses. This review tries to call the attention on synthetic aspects related to the generation of the four-membered heterocyclic ring, published in the last few years, with special accent in stereoselective synthetic approaches. The compendium will cover methods for achieving diastereo- and enantioselectivity during [2+2] cycloadditions, with the Staudinger reaction still as the first choice method, but also important achievements have been published for the imine-enolate condensation, the carbonylative cycloaddition, and the Kinugasa reaction. Significant success was also obtained in the synthesis of innovative 2-azetidinones through the formation of a single bond. In this respect, the C3-C4 bond formation, through intramolecular cyclization of linear epoxy or halo derivatives, and the carbenoid C-H insertion are among the most effectively exploited procedures. In addition, the adaptation of most procedures to solid-phase methodologies has facilitated the generation of molecular diversity based on the β – lactam skeleton.
Keywords: β-lactams, 2-azetidinones, stereoselective synthesis, chiral auxiliaries, chiral catalysts, memory of chirality
Current Organic Synthesis
Title: An Update on the Synthesis of β-Lactams
Volume: 6 Issue: 3
Author(s): M. Teresa Aranda, Paula Perez-Faginas and Rosario Gonzalez-Muniz
Affiliation:
Keywords: β-lactams, 2-azetidinones, stereoselective synthesis, chiral auxiliaries, chiral catalysts, memory of chirality
Abstract: Because the renewed interest of β – lactams in organic and medicinal chemistry, research in this field continues in producing new appealing progresses. This review tries to call the attention on synthetic aspects related to the generation of the four-membered heterocyclic ring, published in the last few years, with special accent in stereoselective synthetic approaches. The compendium will cover methods for achieving diastereo- and enantioselectivity during [2+2] cycloadditions, with the Staudinger reaction still as the first choice method, but also important achievements have been published for the imine-enolate condensation, the carbonylative cycloaddition, and the Kinugasa reaction. Significant success was also obtained in the synthesis of innovative 2-azetidinones through the formation of a single bond. In this respect, the C3-C4 bond formation, through intramolecular cyclization of linear epoxy or halo derivatives, and the carbenoid C-H insertion are among the most effectively exploited procedures. In addition, the adaptation of most procedures to solid-phase methodologies has facilitated the generation of molecular diversity based on the β – lactam skeleton.
Export Options
About this article
Cite this article as:
Aranda Teresa M., Perez-Faginas Paula and Gonzalez-Muniz Rosario, An Update on the Synthesis of β-Lactams, Current Organic Synthesis 2009; 6 (3) . https://dx.doi.org/10.2174/157017909788921899
DOI https://dx.doi.org/10.2174/157017909788921899 |
Print ISSN 1570-1794 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6271 |
Call for Papers in Thematic Issues
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
Photoswitches for Molecular Recognition
This Special Issue would cover the hot topics on synthesis and chemical and photophysical characterization of new photoswitchable derivatives and their applications on molecular recognition of metabolites and biological active compounds, both in physiological medium and in living cells. Photoswitches are compounds that can change their conformation or properties in ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
Related Articles
-
Alcohol Enhances HIV Infection of Cord Blood Monocyte-Derived Macrophages
Current HIV Research Antigen-specific Immunotherapy in Ovarian Cancer and p53 as Tumor Antigen
Current Pharmaceutical Design Estrogen Receptor Neurobiology and its Potential for Translation into Broad Spectrum Therapeutics for CNS Disorders
Current Molecular Pharmacology Blockade of Renin Angiotensin System in Heart Failure Post-Myocardial Infarction: What is the Best Therapy?
Recent Patents on Cardiovascular Drug Discovery Remyelination in Multiple Sclerosis: The Therapeutic Potential of Neural and Mesenchymal Stem/Progenitor Cells
Current Signal Transduction Therapy The Urokinase Receptor in the Central Nervous System
CNS & Neurological Disorders - Drug Targets Oxidative-Nitrosative Stress as a Contributing Factor to Cardiovascular Disease in Subjects with Diabetes
Current Vascular Pharmacology Receptor Tyrosine Kinases are Signaling Intermediates of G Protein- Coupled Receptors
Current Pharmaceutical Design Expression Profiling of Estrogen Responsive Genes Using Genomic and Proteomic Techniques for the Evaluation of Endocrine Disruptors
Current Pharmacogenomics Interactions of Antimicrobial Peptides with Bacterial Membranes and Membrane Components
Current Topics in Medicinal Chemistry Patent Selections
Recent Patents on Anti-Infective Drug Discovery Role of Connexins and Pannexins in Ischemic Stroke
Current Medicinal Chemistry Inhibitors Targeting the LFA-1/ICAM-1 Cell-Adhesion Interaction: Design and Mechanism of Action
Current Pharmaceutical Design De novo Designed Lipopolysaccharide Binding Peptides: Structure Based Development of Antiendotoxic and Antimicrobial Drugs
Current Medicinal Chemistry Teaching Pharmacogenetics in Low and Middle-Income Countries: Team Based Learning and Lessons Learned at the American University of Beirut
Current Pharmacogenomics and Personalized Medicine Endoplasmic Reticulum Stress-induced Transcriptional Factor CHOP and Cardiovascular Diseases
Current Hypertension Reviews Mechanisms of Action and Chemical-Biological Interactions Between Ozone and Body Compartments: A Critical Appraisal of the Different Administration Routes
Current Drug Therapy Roles of a Novel Molecule ‘Shati’ in the Development of Methamphetamine-Induced Dependence
Current Neuropharmacology Epigenetic Mismatches with Mutated Transcribing Genes at Leukemogenic S-Phase Binding/Start Sites – Potential Targets for Therapy with Enzyme Inhibitors
Current Stem Cell Research & Therapy Use of Ceramides and Related Products for Childhood-Onset Eczema
Recent Patents on Inflammation & Allergy Drug Discovery