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

Susannah Coote; Seidjolo Quenum; David Procter

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

Susannah Coote, Seidjolo Quenum, David Procter

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

34 Citations (SciVal)

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.

Original language	English
Pages (from-to)	5104-5108
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	9
Publication status	Published - 5 May 2011

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https://pubs.rsc.org/en/content/articlelanding/2011/ob/c1ob05710c#!divAbstract

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

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.",

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T1 - Exploiting Sm(ii) and Sm(iii) in SmI2-initiated reaction cascades: application in a tag removal–cyclisation approach to spirooxindole scaffolds

AU - Coote, Susannah

AU - Quenum, Seidjolo

AU - Procter, David

PY - 2011/5/5

Y1 - 2011/5/5

N2 - 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.

AB - 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.

M3 - Article

SN - 1477-0520

VL - 9

SP - 5104

EP - 5108

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

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

Abstract

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