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

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• 作者：Giuseppe Zanoni ; Aless ; ro D’ ; Alfonso ; Alessio Porta ; Lazzaro Feliciani ; Steven P. Nolan ; Giovanni Vidari
• 关键词：Anti-glaucoma drug ; Meyer– ; Schuster rearrangement ; Gold Chemistry ; Prostanoids syntheses ; Total synthesis
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：18 September 2010
• 年：2010
• 卷：66
• 期：38
• 页码：7472-7478
• 全文大小：444 K

文摘

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.