A convenient procedure for the solid-phase synthesis of hydroxamic acids on PEGA resins

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• 作者：Nitin S. Nandurkar^a ; Rico Petersen^a ; Katrine Qvortrup^a ; Vitaly V. Komnatnyy^a ; Kennedy M. Taveras^a ; Sebastian T. Le Quement^a ; Robin Frauenlob^a ; Michael Givskov^b ; Thomas E. Nielsen^a ;   ; ^{ten@kemi.dtu.dk}
• 关键词：Hydroxamic acids ; Solid-phase synthesis ; Hydroxylamine ; HDAC inhibitor ; PEGA resin
• 刊名：Tetrahedron Letters
• 出版年：2011
• 出版时间：28 December 2011
• 年：2011
• 卷：52
• 期：52
• 页码：7121-7124
• 全文大小：1239 K

文摘

An efficient method for the solid-phase synthesis of hydroxamic acids is described. The method comprises the nucleophilic displacement of esters immobilized on PEGA resins with hydroxylamine/sodium hydroxide in isopropanol. The hydroxyaminolysis protocol is compatible with a broad range of PEGA-supported peptide and peptidomimetic esters. The methodology was found to be compatible with two new strategies for the synthesis of solid-supported lactams and diketopiperazines, respectively, both relying on the high inter- and intramolecular reactivity of cyclic N-acyliminium ions with electron-rich aromatics and heteroaromatics, ultimately affording hydroxamic acid derivatives in high purities.