Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media
Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media
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DOI：
10.1021/acs.joc.8b02223
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发表时间：
2018-12-07
影响因子：
3.6
通讯作者：
Emoto, Makoto
中科院分区：
文献类型：
--
作者：
Hirasawa, Shun;Mukai, Ken;Emoto, Makoto
阿扎斯匹灵及其同源物具有独特的螺环核心结构，具有多种生物活性。然而，关于(-)-阿扎斯匹林的化学性质的研究很少，尽管它可能为揭示生物合成途径提供重要的见解。在这里，我们报道了一个九步化学合成阿扎斯匹林类似物的新发现，天然(-)-阿扎斯匹林骨架在中性水介质中容易外消旋。
Azaspirene and related congeners, which possess various biological activities, have a unique spirocyclic core structure. However, there are few studies on the chemical properties of (-)-azaspirene, despite the fact that it may provide important insights into unveiling the biosynthetic pathway. Here, we report a nine-step chemical synthesis of an azaspirene analogue with a new finding that the natural (-)-azaspirene skeleton easily racemizes in neutral aqueous media.