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

doi:10.1016/j.bmcl.2011.02.091

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

Natural Resources and the Environment, School of

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	2327-2329
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	8
DOIs	https://doi.org/10.1016/j.bmcl.2011.02.091
State	Published - Apr 15 2011

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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Biomimetic conversion of (-)-fusoxypyridone and (-)-oxysporidinone to (-)-sambutoxin : Further evidence for the structure of the tricyclic pyridone alkaloid, (-)-fusoxypyridone. / Wijeratne, E. M.Kithsiri; Gunatilaka, A. A.Leslie.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 21, No. 8, 15.04.2011, p. 2327-2329.

Research output: Contribution to journal › Article › peer-review

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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).",

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