Explorations of Stemona Alkaloid-Inspired Analogues: Skeletal Modification and Functional Group Diversification

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• 作者：Kevin J. Frankowski ; Benjamin Neuenswander ; Jeffrey Aubé
• 刊名：Journal of Combinatorial Chemistry
• 出版年：2008
• 出版时间：September 8, 2008
• 年：2008
• 卷：10
• 期：5
• 页码：721-725
• 全文大小：223K
• 年卷期：v.10,no.5(September 8, 2008)
• ISSN：1520-4774

文摘

A tandem Diels−Alder/Schmidt reaction provided an efficient route for the exploration of unnatural Stemona alkaloid analogues. Thus, a series of tricyclic scaffolds were efficiently prepared and then elaborated into seven sets of functionalized analogues. These derivatives incorporated appended heterocycles, such as indoles and quinolines, or other diversity-incorporating moieties such as carbamates and amines. Both the scaffold-generation sequence and the diversification steps could be manipulated to provide regio- and diastereochemically pure products.