Biomimetic conversion of (-)-fusoxypyridone and (-)-oxysporidinone to (-)-sambutoxin: Further evidence for the structure of the tricyclic pyridone alkaloid, (-)-fusoxypyridone

E. M.Kithsiri Wijeratne, A. A.Leslie Gunatilaka

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

Biomimetic-type reactions of the tricyclic pyridone alkaloid, (-)-fusoxypyridone [(-)-4,6′-anhydrooxysporidinone] (1), recently encountered in an endophytic strain of Fusarium oxysporum, and (-)-oxysporidinone (2) afforded (-)-sambutoxin (3) and an analogue of 1, identified as (-)-1′(6′)-dehydro-4,6′-anhydrooxysporidinone (4), thus confirming the structure previously proposed for 1 and suggesting that 1-3 bear the same relative stereochemistry. Oxidation of 4 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) yielded a hitherto unknown sambutoxin analogue, (-)-4,2′-anhydrosambutoxin (5).

Original languageEnglish (US)
Pages (from-to)2327-2329
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume21
Issue number8
DOIs
StatePublished - Apr 15 2011

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Keywords

  • (-)-4,2′-Anhydrosambutoxin
  • (-)-Fusoxypyridone
  • (-)-Oxyporidinone
  • 4-Hydroxy-2-pyridone alkaloids
  • Biomimetic reaction

ASJC Scopus subject areas

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

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