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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.

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.
AuthorsSusannah C Coote, Seidjolo Quenum, David J Procter
JournalOrganic & biomolecular chemistry (Org Biomol Chem) Vol. 9 Issue 14 Pg. 5104-8 (Jul 21 2011) ISSN: 1477-0539 [Electronic] England
PMID21617813 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Iodides
  • Spiro Compounds
  • Samarium
Topics
  • Cyclization
  • Iodides (chemistry)
  • Molecular Structure
  • Samarium (chemistry)
  • Spiro Compounds (chemical synthesis, chemistry)
  • Stereoisomerism

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