{"title":"Intramolecular cycloaddition of nitrones in total synthesis of natural products","authors":"Satoshi Yokoshima","doi":"10.1039/d4np00062e","DOIUrl":null,"url":null,"abstract":"<div><div>Covering 2015 to 2024</div></div><div><div>Cycloaddition of nitrones with alkenes forms isoxazolidines, which are five-membered heterocycles containing nitrogen and oxygen atoms. This transformation functionalizes alkenes by forming C–C and C–O bonds. The N–O bond in the resultant isoxazolidines is easily cleaved. Additionally, when the cycloaddition is carried out intramolecularly, the regioselectivity of the reaction is influenced by the tether connecting the nitrone and alkene and can differ from the selectivity governed by frontier molecular orbital interaction. These features make the intramolecular cycloaddition of nitrones attractive in the synthesis of complex molecules. In this review, we discuss the intramolecular cycloaddition of nitrones used in the total synthesis of natural products.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"42 7","pages":"Pages 1071-1090"},"PeriodicalIF":10.6000,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Natural Product Reports","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0265056825000303","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
Covering 2015 to 2024
Cycloaddition of nitrones with alkenes forms isoxazolidines, which are five-membered heterocycles containing nitrogen and oxygen atoms. This transformation functionalizes alkenes by forming C–C and C–O bonds. The N–O bond in the resultant isoxazolidines is easily cleaved. Additionally, when the cycloaddition is carried out intramolecularly, the regioselectivity of the reaction is influenced by the tether connecting the nitrone and alkene and can differ from the selectivity governed by frontier molecular orbital interaction. These features make the intramolecular cycloaddition of nitrones attractive in the synthesis of complex molecules. In this review, we discuss the intramolecular cycloaddition of nitrones used in the total synthesis of natural products.
期刊介绍：
Natural Product Reports (NPR) serves as a pivotal critical review journal propelling advancements in all facets of natural products research, encompassing isolation, structural and stereochemical determination, biosynthesis, biological activity, and synthesis.
With a broad scope, NPR extends its influence into the wider bioinorganic, bioorganic, and chemical biology communities. Covering areas such as enzymology, nucleic acids, genetics, chemical ecology, carbohydrates, primary and secondary metabolism, and analytical techniques, the journal provides insightful articles focusing on key developments shaping the field, rather than offering exhaustive overviews of all results.
NPR encourages authors to infuse their perspectives on developments, trends, and future directions, fostering a dynamic exchange of ideas within the natural products research community.
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