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有机催化的高对映选择性取代 3-(1-对甲苯磺酰基)吲哚与氧化吲哚,首次实现 (+)-三古鲁特 B 的全合成。

Organocatalytic Highly Enantioselective Substitution of 3-(1-Tosylalkyl)indoles with Oxindoles Enables the First Total Synthesis of (+)-Trigolutes B.

机构信息

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China), Fax: (+86) 551-360-6266 http://staff.ustc.edu.cn/∼gonglz/index.htm.

Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) (P. R. China).

出版信息

Chemistry. 2015 Jun 1;21(23):8389-93. doi: 10.1002/chem.201500349. Epub 2015 Apr 27.

Abstract

A highly enantioselective organocatalytic substitution of 3-(1-tosylalkyl)indoles with oxindoles has been established by using chiral bifunctional organocatalysts, providing an efficient entry to multiply functionalized 3,3'-disubstituted oxindoles, and was exploited as the key step to enable the first asymmetric total synthesis of optically pure (+)-trigolutes B to be accomplished in a concise manner, within seven steps with an 18% overall yield.

摘要

一种高对映选择性的 3-(1-对甲苯磺酰烷基)吲哚与氧化吲哚的取代反应已经通过使用手性双功能有机催化剂得以建立,这为多官能化的 3,3'-二取代氧化吲哚提供了一种有效的合成途径,并且该反应被用作关键步骤,使得 (+)-三叶豆苷 B 的首次不对称全合成以简洁的方式在七个步骤内完成,总收率为 18%。

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