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Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

Berthet, Mathéo ; Cheviet, Thomas ; Dujardin, Gilles ; Parrot, Isabelle ; Martinez, Jean

Chemical reviews, 2016-12, Vol.116 (24), p.15235-15283 [Periódico revisado por pares]

United States: American Chemical Society

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Título:
Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry
Autor: Berthet, Mathéo ; Cheviet, Thomas ; Dujardin, Gilles ; Parrot, Isabelle ; Martinez, Jean
Assuntos: Amino acids ; Anti-Infective Agents ; Anti-Infective Agents - chemical synthesis ; Anti-Inflammatory Agents, Non-Steroidal ; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis ; Antineoplastic Agents ; Antineoplastic Agents - chemical synthesis ; Benzazepines ; Benzazepines - chemical synthesis ; beta-Lactams ; beta-Lactams - chemical synthesis ; Biological activity ; Carbohydrates ; Carbohydrates - chemical synthesis ; Chemical compounds ; Chemical Sciences ; Chemical synthesis ; Cyclization ; Cycloaddition Reaction ; Isoxazoles ; Isoxazoles - chemical synthesis ; Isoxazoles - chemistry ; Isoxazolidines ; Nucleosides ; Nucleosides - chemical synthesis ; Optimization ; Organic chemistry ; Oxazines ; Oxazines - chemical synthesis ; Oxidation-Reduction ; Peptide Nucleic Acids ; Peptide Nucleic Acids - chemical synthesis ; Peptidomimetics ; Peptidomimetics - chemical synthesis ; Pyridones ; Pyridones - chemical synthesis ; Scaffolds ; Steroids ; Synthesis (chemistry)
É parte de: Chemical reviews, 2016-12, Vol.116 (24), p.15235-15283
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Descrição: The isoxazolidine ring represents one of the privileged structures in medicinal chemistry, and there have been an increasing number of studies on isoxazolidine and isoxazolidine-containing compounds. Optimization of the 1,3-dipolar cycloaddition (1,3-DC), original methods including electrophilic or palladium-mediated cyclization of unsaturated hydroxylamine, has been developed to obtain isoxazolidines. Novel reactions involving the isoxazolidine ring have been highlighted to accomplish total synthesis or to obtain bioactive compounds, one of the most significant examples being probably the thermic ring contraction applied to the total synthesis of (±)-Gelsemoxonine. The unique isoxazolidine scaffold also exhibits an impressive potential as a mimic of nucleosides, carbohydrates, PNA, amino acids, and steroid analogs. This review aims to be a comprehensive and general summary of the different isoxazolidine syntheses, their use as starting building blocks for the preparation of natural compounds, and their main biological activities.
Editor: United States: American Chemical Society
Idioma: Inglês

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Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry

Berthet, Mathéo ; Cheviet, Thomas ; Dujardin, Gilles ; Parrot, Isabelle ; Martinez, Jean

United States: American Chemical Society

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