关于衍生生物碱螺旋卡尔卡里定A和B的研究——可能的生物合成意义。
Studies Towards the -derived Alkaloids Spirocalcaridine A and B - Possible Biosynthetic Implications.
作者信息
Koswatta Panduka B, Das Jayanta, Yousufuddin Muhammed, Lovely Carl J
机构信息
Department of Chemistry and Biochemistry, The University of Texas at Arlington, 700 Planetarium Place, Arlington, Texas 76019-0065, USA, , Homepage: http://www.uta.edu/chemistry/faculty/directory/Lovely.php.
Center for Nanostructured Materials, The University of Texas at Arlington, 700 Planetarium Place, Arlington, TX 76019-0065, USA.
出版信息
European J Org Chem. 2015 Apr;2015(12):2603-2613. doi: 10.1002/ejoc.201403650.
An exploration of an abiotic approach to spirocalcaridines A and B is described centered on electrophile-induced dearomatizing spirocyclization of aryl enyne derivatives. Elaboration of the α-iodoenone via an Ullmann-like, copper-catalyzed amidation provided a formamide which upon treatment with methylamine undergoes a dienol-arene rearrangement, providing the corresponding kealiinine-like framework. This observation suggests a possible biosynthetic links between the spirocalcaridines and the naphthimidazole group of alkaloids.
本文描述了一种非生物合成方法来制备螺旋卡尔啶A和B，该方法以亲电试剂诱导的芳基烯炔衍生物的去芳构化螺环化反应为核心。通过类似乌尔曼反应的铜催化酰胺化反应对α-碘代烯酮进行修饰，得到一种甲酰胺，该甲酰胺在用甲胺处理时会发生二烯醇-芳烃重排，从而提供相应的类似凯阿利宁的骨架。这一观察结果表明螺旋卡尔啶与萘并咪唑类生物碱之间可能存在生物合成联系。
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