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

详细信息    查看全文

• 作者：E.M. Kithsiri Wijeratne^a ; A.A. Leslie Gunatilaka ; ^a ; ^{leslieg@ag.arizona.edu}
• 关键词：Biomimetic reaction ; 4-Hydroxy-2-pyridone alkaloids ; (&#x2212 ; )-Fusoxypyridone ; (&#x2212 ; )-Oxyporidinone ; (&#x2212 ; )-4 ; 2′ ; -Anhydrosambutoxin
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2011
• 出版时间：15 April 2011
• 年：2011
• 卷：21
• 期：8
• 页码：2327-2329
• 全文大小：324 K

文摘

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).