One-pot synthesis of a natural product inspired pyrrolocoumarine compound collection by means of an intramolecular 1,3-dipolar cycloaddition as key step

被引：16

作者：

Vidadala, Srinivasa Rao ^{[1
]}

Waldmann, Herbert ^{[1
,2
]}

机构：

[1] Max Planck Inst Mol Physiol, Abt Chem Biol, D-44227 Dortmund, Germany

[2] Tech Univ Dortmund, Fak Chem & Chem Biol, Chem Biol, D-44221 Dortmund, Germany

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 23期

关键词：

Biology oriented synthesis; Pyrrolocoumarine; 1,3-Dipolar cycloaddition; One-pot synthesis; Azomethine ylide; CATALYTIC ENANTIOSELECTIVE SYNTHESIS; AZOMETHINE YLIDES; DISCOVERY; INHIBITORS;

D O I：

10.1016/j.tetlet.2015.01.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, sequential and efficient one-pot synthesis of natural product inspired chromeno[3,4-b]pyrrol-4(3H)-ones is described. The one-pot reaction sequence consists of N-Boc deprotection of a N-substituted Boc-glycine O-aryl ester embodying an ortho-alkyne substituent, azomethine ylide generation with an aldehyde, subsequent intramolecular 1,3-dipolar cycloaddition with the alkyne followed by oxidative aromatization. This synthesis method gives efficient access to a collection of highly substituted diverse pyrrolocoumarines. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：3358 / 3360

页数：3

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