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Four-Component Assembly of Natural-Product-Like Ring-Fused Isoquinuclidines
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
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2013 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 33, 7476-7479 p.Article in journal (Refereed) Published
Abstract [en]

A four-component reaction between formyl-substituted 2-pyridones, aldehydes, amines, and activated alkenes has been developed. The resulting products are ring-fused natural-product-like isoquinuclidines. Three carbon–carbon bonds, two carbon–nitrogen bonds, and four or five stereocentres are formed in the reaction with overall product yields in the range 23–67 %. In most cases a single diastereomer was obtained. An intramolecular version of the reaction yielded analogues of the multi-ring-fused natural product catharanthine in a single step.

Place, publisher, year, edition, pages
John Wiley & Sons, 2013. no 33, 7476-7479 p.
Keyword [en]
Multicomponent reactions; Natural products, Fused-ring systems, Nitrogen­ heterocycles
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:umu:diva-82338DOI: 10.1002/ejoc.201301371OAI: oai:DiVA.org:umu-82338DiVA: diva2:660686
Available from: 2013-10-30 Created: 2013-10-30 Last updated: 2017-12-06Bibliographically approved

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Sellstedt, MagnusDang, The HungPrasad, G. KrishnaSauer, UweAlmqvist, Fredrik
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