Catalytic Enantioselective Total Synthesis of Riccardiphenol B

被引：8

作者：

Cottet, Pierre ^{[1
]}

Bleschke, Christian ^{[1
]}

Capdevila, Montse Guiteras ^{[1
]}

Tissot, Matthieu ^{[1
]}

Alexakis, Alexandre ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, Quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 03期

基金：

新加坡国家研究基金会; 瑞士国家科学基金会;

关键词：

asymmetric catalysis; enolate trapping; Michael addition; quaternary stereocenters; riccardiphenol B; sesquiterpenes; total synthesis; ASYMMETRIC CONJUGATE ADDITION; CROSS-COUPLING REACTIONS; GRIGNARD-REAGENTS; CONSTRUCTION; VINYL; ARYL; DERIVATIVES; LIVERWORT; CENTERS; LIGANDS;

D O I：

10.1002/adsc.201500928

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The first catalytic enantioselective total synthesis of riccardiphenol B, a sesquiterpene derivative isolated from a Japanese collection of the liver-wort Riccardia crassa, has been achieved. A copper-catalyzed asymmetric conjugate addition of trimethylaluminum was used at an early stage to generate the quaternary stereogenic center with high enantiomeric excess. The corresponding sterically en-cumbered aluminum enolate was directly trapped with an alpha-amino ether, allowing after oxidation, the release of a key intermediate in the total synthesis of the target natural product.

引用

页码：417 / 425

页数：9

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