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

Bioorg Med Chem Lett. 2011 Apr 15;21(8):2327-9. doi: 10.1016/j.bmcl.2011.02.091. Epub 2011 Mar 16.

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).

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkaloids / chemistry*
  • Biomimetics
  • Fusarium / chemistry
  • Heterocyclic Compounds, 3-Ring / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Mycotoxins / chemistry*
  • Oxidation-Reduction
  • Pyridones / chemistry*
  • Stereoisomerism

Substances

  • Alkaloids
  • Heterocyclic Compounds, 3-Ring
  • Mycotoxins
  • Pyridones
  • oxysporidinone
  • sambutoxin