Iron(III) chloride-catalyzed synthesis of 3-carboxy-2,5-disubstituted furans from γ-alkynyl aryl- and alkylketones

被引：12

作者：

Golonka, Alexander N. ^{[1
]}

Schindler, Corinna S. ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Willard Henry Dow Lab, 930 North Univ Ave, Ann Arbor, MI 48109 USA

来源：

TETRAHEDRON | 2017年 / 73卷 / 29期

关键词：

Iron(III) chloride; Furan; Heterocycle; Lewis acid catalysis; Cembrane natural products; SELECTIVE SYNTHESIS; BUILDING-BLOCKS; LOPHOTOXIN; CYCLOISOMERIZATION; CEMBRANOLIDE; PUKALIDE; HALIDES; BASE;

D O I：

10.1016/j.tet.2017.04.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild, catalytic method for the synthesis of 3-carboxy-2,5-disubstituted furans is reported proceeding via a 5-exo-dig cycloisomerization reaction. The iron(III) chloride-catalyzed transformation of aryl- and alkyl beta-ketoesters enables synthetic access to functionalized furan core structures found in many natural products and complex molecules of biological importance. The method described herein, represents a mild and efficient alternative to currently available reaction protocols. (C) 2017 Elsevier Ltd. All rights reserved

引用

页码：4109 / 4114

页数：6

共 44 条

[1] Highly substituted furans from 2-propynyl-1,3-dicarbonyls and organic halides or triflates via the oxypalladation-reductive elimination domino reaction [J].