Three-Step Synthesis of (卤)-Preussin from Decanal

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• 作者：Isac G. Rosset ; Rafael M. P. Dias ; Vagner D. Pinho ; Antonio C. B. Burtoloso
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：July 18, 2014
• 年：2014
• 卷：79
• 期：14
• 页码：6748-6753
• 全文大小：334K
• ISSN：1520-6904

文摘

A straightforward and stereoselective synthesis of the alkaloid preussin is described starting from decanal and diethyl 3-diazo-2-oxopropylphosphonate. The key steps are an aza-Michael reaction from an 伪,尾-unsaturated diazoketone followed by a highly stereoselective Cu-catalyzed ylide formation and then a [1,2]-Stevens rearrangement. This strategy is feasible for extension to preussin analogues, demonstrating its utility for the rapid construction of all-cis-substituted pyrrolidines.