Biomimetic synthesis of xuxuarines Eα and Eβ: Structure revision of Rzedowskia bistriterpenoids

Neil E. Jacobsen, E. M.Kithsiri Wijeratne, Joaquim Corsino, Maysa Furlan, Vanderlan da S. Bolzani, A. A.Leslie Gunatilaka

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

Reaction of pristimerin with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) resulted in a biomimetic-type coupling leading to xuxuarines Eα and Eβ and not the previously reported Rzedowskia bistriterpenoids I and II suggesting that the structures proposed for these natural products need revision. A product obtained in this reaction by an unusual Diels-Alder addition followed by retro-Diels-Alder-type elimination was characterized as pristimerin dicyanophenalenedione. Complete 1H, and 13C NMR spectral assignments of xuxuarines Eα and Eβ have been made by the application of 1D and 2D NMR techniques.

Original languageEnglish (US)
Pages (from-to)1884-1889
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number4
DOIs
StatePublished - Feb 15 2008

Keywords

  • Biomimetic synthesis
  • Biscelastroloids
  • DDQ oxidation
  • Rzedowskia bistriterpenoids
  • Xuxuarine Eα
  • Xuxuarine Eβ

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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