Convergent, Fit-For-Purpose, Kilogram-Scale Synthesis of a 5-Lipoxygenase Inhibitor

详细信息    查看全文

• 作者：St茅phane G. Ouellet ; Danny Gauvreau ; Mark Cameron ; Sarah Dolman ; Louis-Charles Campeau ; Gregory Hughes ; Paul D. O鈥橲hea ; Ian W. Davies
• 刊名：Organic Process Research & Development
• 出版年：2012
• 出版时间：February 17, 2012
• 年：2012
• 卷：16
• 期：2
• 页码：214-219
• 全文大小：273K
• 年卷期：v.16,no.2(February 17, 2012)
• ISSN：1520-586X

文摘

Process research and development of a synthetic route towards a novel 5-lipoxygenase inhibitor is described. The synthetic route provided 1 in 27% yield in nine steps (seven steps in the longest linear sequence) and was performed on kilogram scale. The synthesis began with the preparation of the coumarin core via an efficient von Pechmann condensation. The triazole fragment was obtained via a regioselective copper-catalyzed [3 + 2] cycloaddition between a chiral alkyne and the coumarin azide.