Transition-Metal-Free Synthesis of a Known Intermediate in the Formal Synthesis of (-)-Steganacin

被引：6

作者：

Augros, David ^{[1
]}

Yalcouye, Boubacar ^{[1
]}

Choppin, Sabine ^{[1
]}

Chesse, Matthieu ^{[1
]}

Panossian, Armen ^{[1
]}

Leroux, Frederic R. ^{[1
]}

机构：

[1] Univ Strasbourg, CNRS, LCM UMR 7509, 25 Rue Becquerel, F-67087 Strasbourg, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 03期

关键词：

Arynes; Asymmetric synthesis; Natural products; Organolithium species; Chirality; ASYMMETRIC TOTAL-SYNTHESIS; BIARYL COUPLING REACTION; STEREOSELECTIVE REACTIONS; ABSOLUTE-CONFIGURATION; TRIFLUOROACETIC-ACID; STEGANACIN CONGENERS; ANTITUBULIN ACTIVITY; AROMATIC REACTIVITY; NATURAL-PRODUCTS; CHIRAL BIARYL;

D O I：

10.1002/ejoc.201601239

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The formal synthesis of the two enantiomers of a natural, axially chiral biaryl, steganacin, is reported. The previously developed atropo-diastereoselective coupling of an aryne and an aryllithium ("aryne coupling") allows for this synthesis. In each step, the axial configuration of the biaryl could be maintained. The key intermediate, identified previously, was accessed without using transition metals, which demonstrates the potential of the aryne coupling reaction as a complementary or alternative to transition-metal-catalyzed coupling reactions.

引用

页码：497 / 503

页数：7

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