{"title":"One-Pot Synthesis of Semisaturated Fused Polycyclic Iminosugars by a Diels-Alder Reaction","authors":"Song Xie, jilai Wu, Likai Zhou, Chao Wei, Xiaoliu Li, Hua Chen","doi":"10.1002/ejoc.202401005","DOIUrl":null,"url":null,"abstract":"Abstract: A series of semi-saturated fused polycyclic iminosugars were synthesized by one-pot stereoselective three-component reactions of D-ribose tosylate, aniline and cycloenones under heating conditions. The N-aryl enamine derived from an iminium ion is the key intermediate for the reaction. In this way, various novel complex fused iminosugars were obtained through a normal Diels-Alder mechanism at 80 °C. This strategy will enable the preparation of bioactive iminosugar analogues with structural diversity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"79 1","pages":""},"PeriodicalIF":2.5000,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/ejoc.202401005","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Abstract: A series of semi-saturated fused polycyclic iminosugars were synthesized by one-pot stereoselective three-component reactions of D-ribose tosylate, aniline and cycloenones under heating conditions. The N-aryl enamine derived from an iminium ion is the key intermediate for the reaction. In this way, various novel complex fused iminosugars were obtained through a normal Diels-Alder mechanism at 80 °C. This strategy will enable the preparation of bioactive iminosugar analogues with structural diversity.
期刊介绍：
The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:
Liebigs Annalen
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry.
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