Mild and Efficient Lewis Acid-Promoted Detritylation in the Synthesis of N-Hydroxy Amides: A Concise Synthesis of (-)-Cobactin T

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• 作者：Shyh-Ming Yang ; Bharat Lagu ; Lawrence J. Wilson
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：October 12, 2007
• 年：2007
• 卷：72
• 期：21
• 页码：8123 - 8126
• 全文大小：94K
• 年卷期：v.72,no.21(October 12, 2007)
• ISSN：1520-6904

文摘

An efficient, high-yielding Lewis acid promoted deprotectionof O-trityl hydroxylamine derivatives is described. A rangeof acid-labile protecting groups, such as N-Boc and O-TBS,were tolerated under these mild conditions. The presentmethod is applicable to the synthesis of a broad range ofhydroxylamine derivatives, including N-hydroxy amides(hydroxamic acids), N-hydroxy sulfonamides, and N-hydroxyureas, which often exhibit significant biological activities.An application of this methodology for a concise synthesisof (-)-Cobactin T (18) is also demonstrated.