Facile Synthesis of Spirocyclic Lactams from 尾-Keto Carboxylic Acids

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• 作者：Wei Yang ; Xianyu Sun ; Wenbo Yu ; Rachita Rai ; Jeffrey R. Deschamps ; Lauren A. Mitchell ; Chao Jiang ; Alexander D. MacKerell ; Jr. ; Fengtian Xue
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：June 19, 2015
• 年：2015
• 卷：17
• 期：12
• 页码：3070-3073
• 全文大小：315K
• ISSN：1523-7052

文摘

A facile synthesis of spirocyclic lactams starting from 尾-keto carboxylic acids via a one-pot cascade reaction involving a Curtius rearrangement and an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate is reported. The same conditions have also been used for the generation of fused cyclic lactams with similar good yields. The synthetic value of this method has been demonstrated by efficient synthesis of tetracyclic spirolactam 8 and pentacyclic spirolactam 9.