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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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Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades: application in a tag removal-cyclisation approach to spirooxindole scaffolds. / Coote, Susannah C.; Quenum, Seidjolo; Procter, David J.
In: Organic and Biomolecular Chemistry , Vol. 9, No. 14, 2011, p. 5104-5108.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Coote, SC, Quenum, S & Procter, DJ 2011, 'Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades: application in a tag removal-cyclisation approach to spirooxindole scaffolds', Organic and Biomolecular Chemistry , vol. 9, no. 14, pp. 5104-5108. https://doi.org/10.1039/c1ob05710c

APA

Coote, S. C., Quenum, S., & Procter, D. J. (2011). Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades: application in a tag removal-cyclisation approach to spirooxindole scaffolds. Organic and Biomolecular Chemistry , 9(14), 5104-5108. https://doi.org/10.1039/c1ob05710c

Vancouver

Coote SC, Quenum S, Procter DJ. Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades: application in a tag removal-cyclisation approach to spirooxindole scaffolds. Organic and Biomolecular Chemistry . 2011;9(14):5104-5108. doi: 10.1039/c1ob05710c

Author

Coote, Susannah C. ; Quenum, Seidjolo ; Procter, David J. / Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades : application in a tag removal-cyclisation approach to spirooxindole scaffolds. In: Organic and Biomolecular Chemistry . 2011 ; Vol. 9, No. 14. pp. 5104-5108.

Bibtex

@article{b6cd494ee3924e5f92abf12e8a89eac1,
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.",
keywords = "CYCLATIVE-CAPTURE STRATEGY, FLUOROUS SYNTHESIS, ORGANIC-SYNTHESIS, SOLID-PHASE, SPIROTRYPROSTATIN-B, SAMARIUM DIIODIDE, PUMMERER REACTION, (-)-SPIROTRYPROSTATIN B, N-HETEROCYCLES, SEPARATION",
author = "Coote, {Susannah C.} and Seidjolo Quenum and Procter, {David J.}",
year = "2011",
doi = "10.1039/c1ob05710c",
language = "English",
volume = "9",
pages = "5104--5108",
journal = "Organic and Biomolecular Chemistry ",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "14",

}

RIS

TY - JOUR

T1 - Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades

T2 - application in a tag removal-cyclisation approach to spirooxindole scaffolds

AU - Coote, Susannah C.

AU - Quenum, Seidjolo

AU - Procter, David J.

PY - 2011

Y1 - 2011

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.

KW - CYCLATIVE-CAPTURE STRATEGY

KW - FLUOROUS SYNTHESIS

KW - ORGANIC-SYNTHESIS

KW - SOLID-PHASE

KW - SPIROTRYPROSTATIN-B

KW - SAMARIUM DIIODIDE

KW - PUMMERER REACTION

KW - (-)-SPIROTRYPROSTATIN B

KW - N-HETEROCYCLES

KW - SEPARATION

U2 - 10.1039/c1ob05710c

DO - 10.1039/c1ob05710c

M3 - Journal article

VL - 9

SP - 5104

EP - 5108

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 14

ER -