钯催化的简洁碳氨化方法合成（±）-罂粟碱。

A concise palladium-catalyzed carboamination route to (+/-)-tylophorine.

机构信息

Medicinal Chemistry Department, Albany Molecular Research, Inc. (AMRI), P.O. Box 15098, 26 Corporate Circle, Albany, New York 12212-5098, USA.

出版信息

J Org Chem. 2009 Dec 18;74(24):9554-7. doi: 10.1021/jo902114u.

DOI:10.1021/jo902114u

PMID:19919084

Abstract

A total synthesis of the racemic natural product tylophorine [(+/-)-1] has been demonstrated using the palladium-catalyzed carboamination method developed by Wolfe and co-workers. In this case, an electron-rich aryl bromide 18 was prepared in four steps and subjected to palladium-catalyzed Wolfe carboamination conditions with olefinic carbamate 7 to provide the racemic 2-(arylmethyl)pyrrolidine (+/-)-19 in good yield and was further elaborated to racemic tylophorine. This application of the Wolfe carboamination protocol as a key step to construct a natural product provides further evidence of the utility of the method.

摘要

沃尔夫（Wolfe）及其同事开发的钯催化碳氨化方法已被证明可用于全合成外消旋天然产物替洛福林[(+/-)-1]。在这种情况下，通过四步反应制备了富电子芳基溴化物 18，并在钯催化的沃尔夫碳氨化条件下与烯属氨基甲酸酯 7 反应，以良好的收率得到外消旋 2-(芳甲基)吡咯烷(+/-)-19，并进一步衍生为外消旋替洛福林。沃尔夫碳氨化方案作为构建天然产物的关键步骤的这种应用进一步证明了该方法的实用性。