The Meyer-Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost

被引：35

作者：

Zanoni, Giuseppe ^{[1
]}

D'Alfonso, Alessandro ^{[1
]}

Porta, Alessio ^{[1
]}

Feliciani, Lazzaro ^{[2
]}

Nolan, Steven P. ^{[3
]}

Vidari, Giovanni ^{[1
]}

机构：

[1] Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy

[2] Sifavitor Srl Mairano di Casaletto Lodigiano, I-26852 Lodi, Italy

[3] Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland

来源：

TETRAHEDRON | 2010年 / 66卷 / 38期

关键词：

Anti-glaucoma drug; Meyer-Schuster rearrangement; Gold Chemistry; Prostanoids syntheses; Total synthesis; CATALYSIS;

D O I：

10.1016/j.tet.2010.07.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold(I) mediated Meyer Schuster rearrangement for the installation of the 'lower' side chain of prostaglandins and their analogs has been developed. This Au-mediated rearrangement, featuring a low catalyst loading and mild reaction conditions, has been demonstrated to be an efficient alternative to the standard Horner-Wadsworth-Emmons reaction in prostaglandin chemistry. Moreover, the present results provide a new synthetic process leading to pharmacologically active prostanoids: Latanoprost and Bimatoprost, that continue to hold key positions in the anti-glaucoma drug market. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：7472 / 7478

页数：7

共 24 条

[1] Alternative synthetic methods through new developments in catalysis by gold [J].