通过选择性C-H和C-C键插入反应对(+)-鸭脚树叶碱进行汇聚式对映选择性合成。
A convergent and enantioselective synthesis of (+)-amurensinine via selective C-H and C-C bond insertion reactions.
作者信息
Tambar Uttam K, Ebner David C, Stoltz Brian M
机构信息
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
出版信息
J Am Chem Soc. 2006 Sep 13;128(36):11752-3. doi: 10.1021/ja0651815.
Abstract
A convergent and enantioselective synthesis of the natural product amurensinine is described. The synthetic strategy takes advantage of mild and selective C-H and C-C bond insertion reactions, in addition to the palladium-catalyzed aerobic oxidative kinetic resolution recently developed in these laboratories.
摘要
本文描述了天然产物木兰辛宁的对映选择性汇聚合成。该合成策略利用了温和且选择性的C-H和C-C键插入反应，以及最近在这些实验室中开发的钯催化需氧氧化动力学拆分反应。
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Angew Chem Int Ed Engl. 2001 Oct 15;40(20):3810-3813. doi: 10.1002/1521-3773(20011015)40:20<3810::AID-ANIE3810>3.0.CO;2-8.
2
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