Cu/Mn Co-oxidized Cyclization for the Synthesis of Highly Substituted Pyrrole Derivatives from Amino Acid Esters: A Strategy for the Biomimetic Syntheses of Lycogarubin C and Chromopyrrolic Acid

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• 作者：Nini Zhou ; Tao Xie ; Lin Liu ; Zhixiang Xie
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：July 3, 2014
• 年：2014
• 卷：79
• 期：13
• 页码：6061-6068
• 全文大小：412K
• ISSN：1520-6904

文摘

An effective and concise approach to synthesis of tetrasubstituted pyrroles from readily available amino acid esters by the promotion of Cu(OAc)₂ in conjunction with Mn(OAc)₃ has been developed. This reaction proceeds through multiple dehydrogenations, deamination, and oxidative cyclization. This oxidized system tolerates substrates bearing various electron-donating or electron-withdrawing groups. With this methodology, several key intermediates of natural products have been effectively prepared, and the total syntheses of lycogarubin C and chromopyrrolic acid have been completed in high efficiency.