A dipolar cycloaddition approach toward the kopsifoline alkaloid framework
A dipolar cycloaddition approach toward the kopsifoline alkaloid framework
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DOI：
10.1016/j.tet.2007.01.064
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发表时间：
2007-06-25
期刊：
影响因子：
2.1
通讯作者：
Padwa, Albert
中科院分区：
文献类型：
--
作者：
Hong, Xuechuan;France, Stefan;Padwa, Albert
以金属催化的多米诺反应为关键步骤，通过Rh（II）催化的重氮酮酯与吲哚π键的1，3-偶极环加成反应，得到一个羰基叶立德偶极，从而构建了一个kopsifoline生物碱家族的杂环骨架.开环得到的1，3-偶极环加合物，然后通过还原性脱羟基步骤导致形成关键的甲硅烷基烯醇醚所需的最终F-环关闭的kopsifoline骨架。(C)2007爱思唯尔有限公司保留所有权利。
Using a metal-catalyzed domino reaction as the key step, the heterocyclic skeleton of the kopsifoline alkaloid family was constructed by a 1,3-dipolar cycloaddition of a carbonyl ylide dipole derived from a Rh(II)-catalyzed reaction of a diazo ketoester across the indole pi-bond. Ring opening of the resulting 1,3-dipolar cycloadduct followed by a reductive dehydroxylation step resulted in the formation of a critical silyl enol ether necessary for the final F-ring closure of the kopsifoline skeleton. (C) 2007 Elsevier Ltd. All rights reserved.