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

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

3 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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10.1016/j.bmcl.2011.02.091

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

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).",

keywords = "(-)-4,2′-Anhydrosambutoxin, (-)-Fusoxypyridone, (-)-Oxyporidinone, 4-Hydroxy-2-pyridone alkaloids, Biomimetic reaction",

author = "Wijeratne, {E. M.Kithsiri} and Gunatilaka, {A. A.Leslie}",

note = "Funding Information: This work was supported by a grant from the National Cancer Institute (Grant No. R01CA090265-06A1 ). We are also thankful to Dr. N. P. D. Nanayakkara (University of Mississippi) for providing samples and copies of spectroscopic data of 2 and 3 .",

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AU - Gunatilaka, A. A.Leslie

N1 - Funding Information: This work was supported by a grant from the National Cancer Institute (Grant No. R01CA090265-06A1 ). We are also thankful to Dr. N. P. D. Nanayakkara (University of Mississippi) for providing samples and copies of spectroscopic data of 2 and 3 .

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N2 - 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).

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

Abstract

Keywords

ASJC Scopus subject areas

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