Concise Total Synthesis of Lundurines A-C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization

被引：85

作者：

Kirillova, Mariia S. ^{[1
]}

Muratore, Michael E. ^{[1
]}

Dorel, Ruth ^{[1
]}

Echavarren, Antonio M. ^{[1
,2
]}

机构：

[1] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Av Paisos Catalans 16, Tarragona 43007, Spain

[2] Univ Rovira & Virgili, Dept Quim Organ & Analit, C Marcelli Domingo S-N, E-43007 Tarragona, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 11期

基金：

欧洲研究理事会;

关键词：

REVERSE ENE REACTION; INDOLE ALKALOIDS; STEREOGENICITY TRANSFER; HYDROGEN SHIFT; KOPSIA-TENUIS; (+/-)-LUNDURINE; STEREOCHEMISTRY; REARRANGEMENTS; (-)-LUNDURINE; STRATEGY;

D O I：

10.1021/jacs.6b01428

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of lundurines A-C has been accomplished in racemic and enantiopure forms in 11-13 and 12-14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold(I)-catalyzed alkyne hydroarylation, a cyclopropanation-via formal [3 + 2] cycloaddition/nitrogen extrusion, and a remarkable olefin migration through a vinylcyclopropane retro-ene/ene reaction that streamlines the endgame.

引用

页码：3671 / 3674

页数：4