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 language | English (US) |
|---|---|
| Pages (from-to) | 2327-2329 |
| Number of pages | 3 |
| Journal | Bioorganic and Medicinal Chemistry Letters |
| Volume | 21 |
| Issue number | 8 |
| DOIs | |
| State | Published - 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
Cite this
Wijeratne, E. M. K., & Gunatilaka, A. A. L. (2011). Biomimetic conversion of (-)-fusoxypyridone and (-)-oxysporidinone to (-)-sambutoxin: Further evidence for the structure of the tricyclic pyridone alkaloid, (-)-fusoxypyridone. Bioorganic and Medicinal Chemistry Letters, 21(8), 2327-2329. https://doi.org/10.1016/j.bmcl.2011.02.091