Synthesis of the isoxazolo[4,3,2-de]phenanthridinone moiety of the parnafungins.
Synthesis of the isoxazolo[4,3,2-de]phenanthridinone moiety of the parnafungins.
复制标题
帕那芬净异恶唑并[4,3,2-去]菲啶酮部分的合成。
DOI：
10.1021/ol901054r
复制
发表时间：
2009
期刊：
影响因子：
5.2
通讯作者：
Snider,BarryB
中科院分区：
文献类型：
--
作者：
Zhou,Quan;Snider,BarryB
一个实用的路线，不稳定的四环异恶唑并[4，3，2-de]菲啶酮部分的抗真菌parnafungins已开发。通过Suzuki偶联反应制备的2′-羟甲基-2-硝基-3-联苯羧酸甲酯经锌还原得到苯并异恶唑酮，再用MsCl和碱处理，以37−47%的产率生成不稳定的四环环体系。该化合物在CDCl 3中分解为菲啶，在碱水溶液中分解为菲啶N-氧化物。
A practical route to the labile tetracyclic isoxazolo[4,3,2-de]phenanthridinone moiety of the antifungal parnafungins has been developed. Zinc reduction of a methyl 2′-hydroxymethyl-2-nitro-3-biphenylcarboxylate, which was prepared by a Suzuki coupling, afforded a benzisoxazolone that was treated with MsCl and base to generate the labile tetracyclic ring system in 37−47% yield. This compound decomposes to the phenanthridine in CDCl3and the phenanthridineN-oxide in aqueous base.