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

Coote, Susannah C. and Quenum, Seidjolo and Procter, David 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). pp. 5104-5108. ISSN 1477-0520

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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.

Item Type:

Journal Article

Journal or Publication Title:

Organic and Biomolecular Chemistry

Uncontrolled Keywords:

/dk/atira/pure/subjectarea/asjc/1300/1303

Subjects:

?? cyclative-capture strategyfluorous synthesisorganic-synthesissolid-phasespirotryprostatin-bsamarium diiodidepummerer reaction(-)-spirotryprostatin bn-heterocyclesseparationbiochemistryorganic chemistryphysical and theoretical chemistry ??

ID Code:

72305

Deposited By:

ep_importer_pure

Deposited On:

05 Jan 2015 11:32

Refereed?:

Yes

Published?:

Published

Last Modified:

15 Jul 2024 14:57

URI:

https://eprints.lancs.ac.uk/id/eprint/72305