Stereocontrolled Formation of a [4.4]Heterospiro Ring System with Unexpected Inversion of Configuration at the Spirocenter

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• 作者：Zhiqiang Ma ; Lin You ; Chuo Chen
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：82
• 期：1
• 页码：731-736
• 全文大小：419K
• ISSN：1520-6904

文摘

Stereoselective construction of the 1,3-diazaspiro[4.4]nonane core skeleton of massadine and related dimeric pyrrole–imidazole alkaloids is a synthetic challenge. We describe herein the synthesis of all C13/14 diastereomers of this spiro molecule through controlled oxidation and epimerization of the C13 spirocenter under mild acidic conditions.