Divergent total synthesis of (-)-aspidophytine and its congeners via Fischer indole synthesis
Divergent total synthesis of (-)-aspidophytine and its congeners via Fischer indole synthesis
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DOI：
10.1016/j.tet.2012.10.060
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发表时间：
2013-01-07
期刊：
影响因子：
2.1
通讯作者：
Tokuyama, Hidetoshi
中科院分区：
文献类型：
--
作者：
Satoh, Hitoshi;Ueda, Hirofumi;Tokuyama, Hidetoshi
以发散方式完成了（-）-aspidophytine的全合成及其同系物（+）-cimicidine和（+）-cimicine的首次全合成。以取代苯肼和三环氨基酮为原料，通过Fischer吲哚合成法构建了盾子草骨架。Fischer吲哚合成的区域化学强烈地依赖于酸的选择，并且弱酸（例如乙酸）以高选择性提供所需的吲哚啉异构体。(C)2012爱思唯尔有限公司保留所有权利。
A total synthesis of (-)-aspidophytine and the first total syntheses of its congeners, (+)-cimicidine and (+)-cimicine, were accomplished in a divergent manner. Construction of the aspidosperma skeleton was executed by Fischer indole synthesis between substituted phenylhydrazines and tricyclic aminoketone. The regiochemistry of the Fischer indole synthesis was strongly dependent on the choice of acid, and a weak acid, such as acetic acid provided the desired indolenine isomer in high selectivity. (C) 2012 Elsevier Ltd. All rights reserved.