A concise total synthesis of (+)-tetrabenazine and (+)-α- dihydrotetrabenazine

Paek S.-M.; Kim N.-J.; Shin D.; Jung J.-K.; Jung J.-W.; Chang D.-J.; Moon H.; Suh Y.-G.

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A concise total synthesis of (+)-tetrabenazine and (+)-α- dihydrotetrabenazine

机译：（+）-丁苯那嗪和（+）-α-二氢丁苯那嗪的简明全合成

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Highly concise asymmetric total syntheses of (+)-tetrabenazine (1), a drug for the treatment of chorea associated with Huntington's disease, and of (+)α-dihydrotetrabenazine (2), an active metabolite of 1, have been accomplished. Our synthetic route features a trans-selective enol etherification, followed by an unprecedented cation-dependent aza-Claisen rearrangement to establish the carbon framework and two stereogenic centers of tetrabenazine. The syntheses consist of seven steps (34% overall yield) for (+)-2 and eight steps (22% overall yield) for (+)-l.

机译：已完成高度精确的不对称总合成，该合成用于治疗与亨廷顿氏病相关的舞蹈病的药物（+）-丁苯那嗪（1）和一种活性代谢物1（+）α-二氢丁苯那嗪（2）。我们的合成路线以反式选择性烯醇醚化为特征，然后进行空前的阳离子依赖性氮杂-克莱森重排，以建立碳骨架和丁苯那嗪的两个立体生成中心。合成由（+）-2的七个步骤（总产率的34％）和（+）-1的八个步骤（总产率的22％）组成。

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《Chemistry: A European journal》 |2010年第15期|共6页
作者
Paek S.-M.; Kim N.-J.; Shin D.; Jung J.-K.; Jung J.-W.; Chang D.-J.; Moon H.; Suh Y.-G.;
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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
Bentazines; Claisen rearrangement; Rearrangement; Total synthesis;

机译：苯那嗪;克莱森重排;重排;总合成;

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1. A concise total synthesis of (+)-tetrabenazine and (+)-α- dihydrotetrabenazine [J] . Paek S.-M., Kim N.-J., Shin D., Chemistry: A European journal . 2010,第15期

机译：（+）-丁苯那嗪和（+）-α-二氢丁苯那嗪的简明全合成
2. Synthesis and X-ray Analysis of Dihydrotetrabenazine, a Metabolite of Tetrabenazine [J] . Chunyi Liua Zhengping Chena Xiaomin Lia amp, Jie Tanga Molecular Crystals & Liquid Crystals . 2012,第1期

机译：四氢苯哒嗪的代谢物二氢丁苯那嗪的合成与X射线分析
3. Synthesis and X-ray Analysis of Dihydrotetrabenazine, a Metabolite of Tetrabenazine [J] . CHUNYI LIU, ZHENGPING CHEN, XIAOMIN LI Molecular crystals and liquid crystals . 2012,第562期

机译：四氢苯哒嗪的代谢物二氢丁苯那嗪的合成与X射线分析
4. Concise Read-Only Specifications for Better Synthesis of Programs with Pointers [C] . Andreea Costea, Amy Zhu, Nadia Polikarpova, European Joint Conferences on Theory and Practice of Software;European Symposium on Programming . 2020

机译：精简的只读规范，可更好地综合使用指针的程序
5. A modular and concise total synthesis of (+/-)-daurichromenic acid and analogues, and, A new method for the mild and selective mono-dealkylation of tertiary amines. [D] . Hu, Hongjuan. 2005

机译：（+/-）-柔红铬酸及其类似物的模块化简捷全合成，以及一种用于叔胺的轻度和选择性单脱烷基的新方法。
6. Differences in Dihydrotetrabenazine Isomer Concentrations Following Administration of Tetrabenazine and Valbenazine [O] . Heather Skor, Evan B. Smith, Gordon Loewen, 2017

机译：服用川tra嗪和戊苯那嗪后二氢丁苯那嗪异构体浓度的差异
7. Differences in Dihydrotetrabenazine Isomer Concentrations Following Administration of Tetrabenazine and Valbenazine [O] . Heather Skor, Evan B. Smith, Gordon Loewen, 2017

机译：四苯嗪和缬沙嗪施用二氢四甲苯杂嗪异构素浓度的差异

A concise total synthesis of (+)-tetrabenazine and (+)-α- dihydrotetrabenazine

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