通过[2,3] - 迁移史蒂文斯重排反应实现(±)-士的宁胺的形式全合成。
Formal Total Synthesis of (±)-Strictamine by [2,3]-Sigmatropic Stevens Rearrangements.
作者信息
Eckermann Ruben, Breunig Michael, Gaich Tanja
机构信息
Faculty of Chemistry, University of Konstanz, Universitätsstr. 10, 78457, Konstanz, Germany.
Current address: Department of Medicinal Chemistry, University of Minnesota, 2231 Sixth Street SE, Minneapolis, Minnesota, 55455, USA.
出版信息
Chemistry. 2017 Mar 17;23(16):3938-3949. doi: 10.1002/chem.201605361. Epub 2017 Feb 22.
To date, more than 100 congeners of the akuammiline alkaloid family have been isolated. Their signature structural element is a methanoquinolizidine moiety, a cage-like scaffold structurally related to adamantane. The structural variations of the family members originate from oxidative processes that mostly trigger rearrangements of the methanoquinolizidine motif. The family of the akuammiline alkaloids is best represented by strictamine. It bears the least functionalized carbon skeleton of all family members without lacking the signature structural motifs. Herein, we report the formal synthesis of strictamine through a Stevens [2,3]-sigmatropic rearrangement as a key step and the synthetic pitfalls related with its synthesis.
迄今为止， Akuammiline 生物碱家族已分离出 100 多种同系物。它们的标志性结构元素是一个甲氧基喹嗪部分，这是一种与金刚烷结构相关的笼状支架。家族成员的结构变化源于氧化过程，这些过程大多会引发甲氧基喹嗪基序的重排。 Akuammiline 生物碱家族中最具代表性的是 strictamine。它拥有所有家族成员中功能化程度最低的碳骨架，同时又不缺少标志性的结构基序。在此，我们报道了以 Stevens [2,3] - 迁移重排为关键步骤的 strictamine 的形式合成及其合成过程中遇到的问题。
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