Highly Stereoselective and Scalable Synthesis of trans-Fused Octahydrocyclohepta[b]pyrrol-4(1H)-ones via the Aza-Cope-Mannich Rearrangement in Racemic and Enantiopure Forms

被引：16

作者：

Belov, Dmitry S. ^{[1
]}

Lukyanenko, Evgeny R. ^{[1
]}

Kurkin, Alexander V. ^{[1
]}

Yurovskaya, Marina A. ^{[1
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 22期

基金：

俄罗斯基础研究基金会;

关键词：

STEREOCONTROLLED TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; CARBON BOND FORMATION; AMARYLLIDACEAE ALKALOIDS; ASPIDOSPERMA ALKALOIDS; 5,11-METHANOMORPHANTHRIDINE TYPE; COMBINATORIAL LIBRARIES; NUCLEOPHILIC-ADDITION; CYCLIZATION REACTIONS; GRIGNARD-REAGENTS;

D O I：

10.1021/jo301762a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed an efficient and stereo-selective route to trans-fused octahydrocyclohepta[b]pyrrol-4(1H)-ones. The key features of our synthesis include the regioselective epoxide ring-opening of alkynyl oxiranes and a stereoselective aza-Cope-Mannich reaction. The target compounds were prepared in 3-6 steps from commercially available starting materials (61-75% overall yield) with minimal chromatographic purification. We have devised an stereoselective route to target compounds using Shi epoxidation or (R)-1-phenylethylamine as a source of chirality.

引用

页码：10125 / 10134

页数：10

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