A Divergent Route to Eravacycline

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• 作者：Wu-Yan ZhangQinglin Che ; Scott Crawford ; Magnus Ronn ; Nicholas Dunwoody
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 20, 2017
• 年：2017
• 卷：82
• 期：2
• 页码：936-943
• 全文大小：446K
• ISSN：1520-6904

文摘

A convergent route to eravacycline (1) has been developed by employing Michael–Dieckmann cyclization between enone 3 and a fully built and protected left-hand piece (LHP, 2). After construction of the core eravacycline structure, a deprotection reaction was developed, allowing for the isoxazole ring opening and global deprotection to be achieved in one pot. The LHP is synthesized from readily available 4-fluoro-3-methylphenol in six steps featuring a palladium-catalyzed phenyl carboxylation in the last step.