Synthetic study of hetisine-type aconite alkaloids.: Part 3:: Total synthesis of (±)-nominine
Synthetic study of hetisine-type aconite alkaloids.: Part 3:: Total synthesis of (±)-nominine
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DOI：
10.1016/j.tet.2006.04.086
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发表时间：
2006-07-17
期刊：
影响因子：
2.1
通讯作者：
Nakai, Hiroshi
中科院分区：
文献类型：
--
作者：
Muratake, Hideaki;Natsume, Mitsutaka;Nakai, Hiroshi
详细描述了（+/-）-诺米宁（1）的全合成。在前两篇文献的基础上，从中间体7出发，完成了（）-诺米宁的全合成。因此，在通过从7到8的转化形成吡咯烷环之后，通过自由基环化从烯炔前体9形成10来构建C环。随后对C环进行加工，然后形成氮杂双环系统，完成了（+/-）-1的全合成。（+/-）-1的单晶X射线分析明确地证实了其分子结构和外消旋晶体结构。(c)2006爱思唯尔有限公司保留所有权利。
Completion of the total synthesis of (+/-)-nominine (1) is described in detail. Based on the results of the preceding two papers, total synthesis of ()-nominine was accomplished diverging from the intermediate 7. Thus, following pyrrolidine ring formation through transformation from 7 to 8, the C-ring was constructed by radical cyclization to form 10 from the enyne precursor 9. Subsequent elaboration of the C-ring, followed by formation of the azabicyclic ring system, completed a total synthesis of (+/-)-1. Single-crystal X-ray analysis of (+/-)-1 unambiguously confirmed its molecular structure and racemic crystal structure. (c) 2006 Elsevier Ltd. All rights reserved.