Enantioselective synthesis of 2-ethyl-2,3-dihydrobenzofuran carboxylic acid, direct precursor of (+)-efaroxan, from a Baylis-Hillman adduct

被引：48

作者：

Silveira, GPD ^{[1
]}

Coelho, F ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Chem, Dept Organ Chem, BR-13084971 Campinas, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 38期

关键词：

Baylis-Hillman; heterocycles; asymmetric synthesis; dihydrobenzofuran; efaroxan;

D O I：

10.1016/j.tetlet.2005.07.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe herein a new and straightforward enantioselective approach to R-(+)-2-ethyl-2,3-dihydrofuran carboxylic acid, the direct precursor of (+)-efaroxan, an alpha(2) adrenoreceptor antagonist, which is indicated to be used for the treatment of neuro-degenerative diseases (Alzheimer and Parkinson), migraine and type Iota Iota diabetes. Our goal was accomplished using a Baylis-Hillman adduct as starting material. The dihydrobenzofuran acid was obtained in eight steps with an overall yield of 14%. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：6477 / 6481

页数：5

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