紫紫醌A-D的全合成。
Total synthesis of zyzzyanones A-D.
作者信息
Nadkarni Dwayaja H, Murugesan Srinivasan, Velu Sadanandan E
机构信息
Department of Chemistry, University of Alabama at Birmingham, 901 14 Street South, Birmingham, Alabama 35294, USA.
出版信息
Tetrahedron. 2013 May 20;69(20):4105-4113. doi: 10.1016/j.tet.2013.03.052.
Abstract
Zyzzyanones A-D is a group of biologically active marine alkaloids isolated from Australian marine sponge . They contain a unique bispyrroloquinone ring system as the core structure. The first total synthesis of all four zyzzyanones is described here. The synthesis of these alkaloids started from a previously known 6-benzylamino indole-4,7-quinone derivative and involves 6-7 steps. The key step in the synthesis involves the construction of a pyrrole ring in one step using a Mn(OAc) mediated oxidative free radical cyclization reaction of a 6-benzylamino indole-4,7-quinone derivative with 4-benzyloxyphenyl acetaldehyde diethyl acetal in CHCN.
摘要
紫紫醌A - D是从澳大利亚海洋海绵中分离出的一组具有生物活性的海洋生物碱。它们含有独特的双吡咯并醌环系统作为核心结构。本文描述了所有四种紫紫醌的首次全合成。这些生物碱的合成从一种先前已知的6 - 苄基氨基吲哚 - 4,7 - 醌衍生物开始，涉及6至7步反应。合成中的关键步骤是在CHCN中，使用Mn(OAc)介导的6 - 苄基氨基吲哚 - 4,7 - 醌衍生物与4 - 苄氧基苯基乙醛二乙缩醛的氧化自由基环化反应一步构建一个吡咯环。
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