Silyl-enolization-asymmetric Claisen rearrangement of 2-allyloxyindolin-3-one:: enantioselective total synthesis of 3a-hydroxypyrrolo[2,3-b]indoline alkaloid alline
Silyl-enolization-asymmetric Claisen rearrangement of 2-allyloxyindolin-3-one:: enantioselective total synthesis of 3a-hydroxypyrrolo[2,3-b]indoline alkaloid alline
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DOI：
10.1016/j.tetlet.2006.05.124
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发表时间：
2006-07-24
影响因子：
1.8
通讯作者：
Hirayama, Tetsuya
中科院分区：
文献类型：
--
作者：
Kawasaki, Tomomi;Takamiya, Wataru;Hirayama, Tetsuya
以2-(1‘-壬基-3’-氧基)吲哚-3-酮为原料，通过硅烯醇化引发的不对称Claisen重排反应合成了3-(2‘-壬烯基)-3-羟基吲哚-2-酮。通过3-(2‘-壬烯基)-3-羟基吲哚-2-酮的烯丙基部分转化为胺，再经还原环合反应，得到了3-羟基吡咯并[2，3-b]吲哚生物碱(+)-Alline的全合成。(C)2006爱思唯尔有限公司。保留所有权利。
Asymmetric Claisen rearrangement triggered by silyl-enolization of 2-(1'-nonel-3'-yloxy)indolin-3-ones was performed in order to prepare 3-(2'-nonenyl)-3-hydroxyindolin-2-ones. Total synthesis of 3-hydroxypyrrolo[2,3-b]indoline alkaloid, (+)-alline was achieved by transformation of the allylic moiety of 3-(2'-nonenyl)-3-hydroxyindolin-2-one to amine followed by reductive cyclization. (c) 2006 Elsevier Ltd. All rights reserved.