A Biomimetic Route for Construction of the [4+2] and [3+2] Core Skeletons of Dimeric Pyrrole鈥揑midazole Alkaloids and Asymmetric Synthesis of Ageliferins

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• 作者：Xiao Wang ; Xiaolei Wang ; Xianghui Tan ; Jianming Lu ; Kevin W. Cormier ; Zhiqiang Ma ; Chuo Chen
• 刊名：The Journal of the American Chemical Society
• 出版年：2012
• 出版时间：November 14, 2012
• 年：2012
• 卷：134
• 期：45
• 页码：18834-18842
• 全文大小：695K
• 年卷期：v.134,no.45(November 14, 2012)
• ISSN：1520-5126

文摘

The pyrrole鈥搃midazole alkaloids have fascinated chemists for decades because of their unique structures. The high nitrogen and halogen contents and the densely functionalized skeletons make their laboratory synthesis challenging. We describe herein an oxidative method for accessing the core skeletons of two classes of pyrrole鈥搃midazole dimers. This synthetic strategy was inspired by the putative biosynthesis pathways and its development was facilitated by computational studies. Using this method, we have successfully prepared ageliferin, bromoageliferin, and dibromoageliferin in their natural enantiomeric form.