title: Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry.
abstract: 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.
authors.affiliation: Institut des Biomolécules Max Mousseron , IBMM UMR-5247 CNRS, Université de Montpellier, ENSCM, CC17-03, Pl. E. Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Mathéo
authors.initials: M
authors.lastname: Berthet
authors.affiliation: Institut des Biomolécules Max Mousseron , IBMM UMR-5247 CNRS, Université de Montpellier, ENSCM, CC17-03, Pl. E. Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Thomas
authors.initials: T
authors.lastname: Cheviet
authors.affiliation: Institut des Molécules et Matériaux du Mans , IMMM UMR 6283 CNRS, Université du Maine, UFR Sciences et Techniques, Avenue Olivier Messiaen, 72085 Le Mans, France.
authors.forename: Gilles
authors.initials: G
authors.lastname: Dujardin
authors.affiliation: Institut des Biomolécules Max Mousseron , IBMM UMR-5247 CNRS, Université de Montpellier, ENSCM, CC17-03, Pl. E. Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Isabelle
authors.initials: I
authors.lastname: Parrot
authors.affiliation: Institut des Biomolécules Max Mousseron , IBMM UMR-5247 CNRS, Université de Montpellier, ENSCM, CC17-03, Pl. E. Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Jean
authors.initials: J
authors.lastname: Martinez
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D001552:Benzazepines / Q000138:chemical synthesis; D002241:Carbohydrates / Q000138:chemical synthesis; D003500:Cyclization; D061565:Cycloaddition Reaction; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis; D010078:Oxazines / Q000138:chemical synthesis; D010084:Oxidation-Reduction; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis; D057786:Peptidomimetics / Q000138:chemical synthesis; D011728:Pyridones / Q000138:chemical synthesis; D047090:beta-Lactams / Q000138:chemical synthesis
chemical_list: D000890:Anti-Infective Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000970:Antineoplastic Agents; D001552:Benzazepines; D002241:Carbohydrates; D007555:Isoxazoles; D009705:Nucleosides; D010078:Oxazines; D020135:Peptide Nucleic Acids; D057786:Peptidomimetics; D011728:Pyridones; D047090:beta-Lactams