Synthesis of cucurbitine derivatives: facile straightforward approach to methyl 3-amino-4-aryl-1-methylpyrrolydine-3-carboxylates

被引：30

作者：

Blanco-Ania, Daniel ^{[1
]}

Hermkens, Pedro H. H. ^{[2
]}

Sliedregt, Leo A. J. M. ^{[3
]}

Scheeren, Hans W. ^{[1
]}

Rutjes, Floris P. J. T. ^{[1
]}

机构：

[1] Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 AJ Nijmegen, Netherlands

[2] Schering Plough Corp, NL-5340 BH Oss, Netherlands

[3] Solvay Pharmaceut, Sector Discovery Weesp, NL-1380 DA Weesp, Netherlands

来源：

TETRAHEDRON | 2009年 / 65卷 / 27期

关键词：

BETA-LACTAMS; AMINO-ACIDS; YLIDES; ESTERS;

D O I：

10.1016/j.tet.2009.04.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general three- or four-step synthesis of cis- and trans-substituted cucurbitine (3-aminopyrrolidine-3-carboxylic acid) derivatives from methyl 2-nitroacetate is reported. The first step utilizes a Knoevenagel condensation with five different aromatic imines or their corresponding aldehydes to form (Z/E)-mixtotes of alpha-nitro acrylates. The second step gives rise to the pyrrolidine-core structures of the title compounds by a 1,3-dipolar cycloaddition reaction using an azomethine ylide. The last step consists of reduction of the nitro group to yield both diastereoisomers of the corresponding 4-aryl cucurbitine methyl esters. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5393 / 5401

页数：9

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