Convergent, fit-for-purpose, kilogram-scale synthesis of a 5-lipoxygenase inhibitor

…, LC Campeau, G Hughes, PD O'Shea…

Index: Ouellet, Stephane G.; Gauvreau, Danny; Cameron, Mark; Dolman, Sarah; Campeau, Louis-Charles; Hughes, Gregory; O'Shea, Paul D.; Davies, Ian W. Organic Process Research and Development, 2012 , vol. 16, # 2 p. 214 - 219

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Citation Number: 10

Abstract

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 ...