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Radical azidation reactions and their application in the synthesis of alkaloids

Lapointe, Guillaume ; Kapat, Ajoy ; Weidner, Karin ; Renaud, Philippe

In: Pure and Applied Chemistry, 2012, vol. 84, no. 7, p. 1633-1641

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    Titel
    • Radical azidation reactions and their application in the synthesis of alkaloids
    Autor
    • Lapointe, Guillaume. Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland
    • Kapat, Ajoy. Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland
    • Weidner, Karin. Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland
    • Renaud, Philippe. Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland
    Dokumententyp
    • Postprint
    Sprache
    • Englisch
    Veröffentlicht in
    • Pure and Applied Chemistry, 2012, vol. 84, no. 7, p. 1633-1641. De Gruyter
    Andere elektronische Ausgabe
    OAI-PMH-ID
    • oai:doc.rero.ch:292270
    Summary
    Recent advances in radical azidation using sulfonyl azides are presented. For instance, radical carboazidation using α-iodoketones, desulfitative carboazidation, and anti-Markovnikov hydroazidation of alkenes are described. These novel methods tolerate a large number of functional groups and allow the synthesis of organic azides that would be difficult to synthesize otherwise. The transformation of the azides using reductive processes as well as a Schmidt reaction under nonacidic conditions were used to synthesize alkaloids including indolizidine 167B, monomorine I, cylindricine C, and lepadiformine C