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

doi:10.1039/c1ob05710c

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

35 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
DOIs	https://doi.org/10.1039/c1ob05710c
Publication status	Published - 5 May 2011

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Access to Document

10.1039/c1ob05710c

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

Cite this

@article{6c919cf2db4246d1a9d949b7882630cb,

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.",

author = "Susannah Coote and Seidjolo Quenum and David Procter",

year = "2011",

month = may,

day = "5",

doi = "10.1039/c1ob05710c",

language = "English",

volume = "9",

pages = "5104--5108",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

}

TY - JOUR

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.

U2 - 10.1039/c1ob05710c

DO - 10.1039/c1ob05710c

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

UN SDGs

Access to Document

Fingerprint

Cite this