仿生转化（-）-呋咱并吡啶酮和（-）-奥克西孢菌素酮为（-）-山桃菌素：三环吡啶酮生物碱（-）-呋咱并吡啶酮结构的进一步证据。

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

机构信息

Southwest Center for Natural Products Research and Commercialization, Office of Arid Lands Studies, School of Natural Resources and The Environment, College of Agriculture and Life Sciences, The University of Arizona, 250 E. Valencia Road, Tucson, AZ 85706-6800, USA.

出版信息

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

DOI:10.1016/j.bmcl.2011.02.091

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3359017/

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).

摘要

最近在一株内生的尖孢镰刀菌（ Fusarium oxysporum ）中发现了三环吡啶酮生物碱（-）-fusoxypyridone [（-）-4,6'-anhydrooxysporidinone]（1）和（-）oxysporidinone（2）的仿生型反应，生成了（-）-sambutoxin（3）和 1 的类似物，鉴定为（-）-1'（6'）-去氢-4,6'-anhydrooxysporidinone（4），从而证实了以前对 1 提出的结构，并表明 1-3 具有相同的相对立体化学。用 2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）氧化 4 得到了一种 hitherto unknown sambutoxin 类似物，（-）-4,2'-anhydrosambutoxin（5）。

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