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Issue 14, 2011
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Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades: application in a tag removal–cyclisation approach to spirooxindole scaffolds

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Abstract

A tag removal–cyclisation sequence is described that is initiated by reduction using a Sm(II) species and completed by a Sm(III) Lewis acid that is formed in an earlier stage. Therefore, the reaction cascade utilises both oxidation states of a samarium reagent in discrete steps and allows access to privileged, pyrrolidinyl-spirooxindole scaffolds and analogues inspired by the anti-cancer natural product spirotryprostatin A.

Graphical abstract: Exploiting Sm(ii) and Sm(iii) in SmI2-initiated reaction cascades: application in a tag removal–cyclisation approach to spirooxindole scaffolds

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Publication details

The article was received on 14 Feb 2011, accepted on 04 May 2011 and first published on 05 May 2011


Article type: Paper
DOI: 10.1039/C1OB05710C
Citation: Org. Biomol. Chem., 2011,9, 5104-5108
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    Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades: application in a tag removal–cyclisation approach to spirooxindole scaffolds

    S. C. Coote, S. Quenum and D. J. Procter, Org. Biomol. Chem., 2011, 9, 5104
    DOI: 10.1039/C1OB05710C

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