The chemical reactivity of a known anti-psoriasis drug. Part 1: Further insights into the products resulting from oxidative cleavage

Alan M. Jones, Magali M. Lorion, Tomas Lebl, Alexandra M.Z. Slawin, Douglas Philp, Nicholas J. Westwood

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The oxidative cleavage of the known anti-psoriasis drug 1 to give 2 has been reported previously. Due to the importance of accessing medium-sized ring containing systems via oxidative cleavage, this reaction has been revisited revealing additional information about the structure of 2. Alternative reaction products were identified when the reaction was carried out in the presence of water. The conversion of 1 to 2 has also been carried out using ruthenium tetroxide. A detailed variable temperature NMR and computational study of the restricted rotation of the N-aryl ring in 2 is presented.

Original languageEnglish (US)
Pages (from-to)9667-9674
Number of pages8
JournalTetrahedron
Volume66
Issue number51
DOIs
StatePublished - Dec 18 2010

Keywords

  • Heterocycle
  • Macrocycle
  • Mechanism
  • Oxidative fragmentation
  • VT NMR analysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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