Stereoselective synthesis of (±)-tacamonine
Stereoselective synthesis of (±)-tacamonine
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DOI：
10.1016/j.tet.2008.08.049
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发表时间：
2008-11-03
期刊：
影响因子：
2.1
通讯作者：
Lin, Qi-xian
中科院分区：
文献类型：
--
作者：
Ho, Tse-Lok;Lin, Qi-xian
我们报告了一种立体控制的方法，五环吲哚生物碱他卡莫胺通过修改先前的路线使用降冰片二烯提供非色胺部分。通过维持一个桥接体系，Bischler-Napieralski反应的还原步骤继续产生桥接的二醇，其中三个甲基氢原子呈全顺式构型。所有19个骨架碳原子都被完全结合，因此，剩下的步骤就是裂解七元环上的维二醇亚基，并进一步氧化和还原得到的内酰胺醛。(C) 2008 Elsevier Ltd版权所有。
We report a stereocontrolled approach to the pentacyclic indole alkaloid tacamonine by modifying an earlier route using norbornadiene to supply the nontryptamine portion. By maintaining a bridged system the reduction step of the Bischler-Napieralski reaction proceeded to deliver a bridged diol in which three methine hydrogen atoms are in an all-cis configuration. All 19 skeletal carbon atoms are fully incorporated, therefore, the only remaining steps involved cleavage of the vic-diol subunit in the seven-membered ring and further oxidation and reduction of the resulting lactam alclehyde. (C) 2008 Elsevier Ltd. All rights reserved.