Co2(CO)8-catalyzed intramolecular hetero-Pauson-Khand reaction of alkynecarbodiimide: synthesis of (+/-)-physostigmine.
Co2(CO)8-catalyzed intramolecular hetero-Pauson-Khand reaction of alkynecarbodiimide: synthesis of (+/-)-physostigmine.
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DOI：
10.1021/ol052562z
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发表时间：
2006-01
期刊：
影响因子：
5.2
通讯作者：
C. Mukai;T. Yoshida;M. Sorimachi;A. Odani
中科院分区：
文献类型：
--
作者：
C. Mukai;T. Yoshida;M. Sorimachi;A. Odani
本文描述了一种新颖的Co(2)(Co)(8)催化的分子内aza- pauson - khand型反应，以合理的产率生成吡咯[2,3-b]吲哚-2- 1环体系。这是首次报道成功地将Co(2)(Co)(8)应用于异pauson - khand反应。值得注意的是，我们的一种吡咯[2,3-b]吲哚-2- 1衍生物以高度立体选择性的方式转化为吲哚生物碱(+/-)-肉毒碱。
[reaction: see text] Herein we describe a novel Co(2)(CO)(8)-catalyzed intramolecular aza-Pauson-Khand-type reaction of alkynecarbodiimide derivatives affords pyrrolo[2,3-b]indol-2-one ring systems in reasonable yields. This is the first reported Co(2)(CO)(8) successfully applied in the hetero-Pauson-Khand reaction. Significantly, the transformation of one of our pyrrolo[2,3-b]indol-2-one derivatives into the indole alkaloid, (+/-)-physostigmine, was completed in a highly stereoselective manner.