A New Acyl Radical-based Route to the 1,5-Methanoazocino[4,3-b]indole Framework of Uleine and Strychnos Alkaloids
A New Acyl Radical-based Route to the 1,5-Methanoazocino[4,3-b]indole Framework of Uleine and Strychnos Alkaloids
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DOI：
10.1021/jo801998h
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发表时间：
2008-11-21
影响因子：
3.6
通讯作者：
Garcia-Diaz, Davinia
中科院分区：
文献类型：
--
作者：
Bennasar, M. -Lluisa;Roca, Tomas;Garcia-Diaz, Davinia
通过硒酯衍生的2-吲哚酰基分别与5-乙基-1，2，3，6-和3-乙基-1，2，5，6-四氢吡啶6-exo和6-endo环化，合成了C-4或C-12乙基取代的1，5-甲桥偶氮辛并[4，3-B]吲哚，它们构成了乌莱碱生物碱的四环骨架和马钱子属生物碱家族的ABDE亚结构。
C-4 or C-12 ethyl substituted 1,5-methanoazocino[4,3-b]indoles, which constitute the tetracyclic framework of uleine alkaloids as well as the ABDE substructure of the Strychnos alkaloid family, have been synthesized by novel 6-exo and 6-endo cyclizations of selenoester-derived 2-indolylacyl radicals upon 5-ethyl-1,2,3,6- and 3-ethyl-1,2,5,6-tetrahydropyridines, respectively.