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A General Route to Cyclopeptide Alkaloids: Total Syntheses and Biological Evaluation of Paliurines E and F, Ziziphines N and Q, Abyssenine A, Mucronine E, and Analogues
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2009-07-01 , DOI: 10.1002/ejoc.200900122
Mathieu Toumi , Vincent Rincheval , Ashley Young , Danielle Gergeres , Edward Turos , François Couty , Bernard Mignotte , Gwilherm Evano

A full account of the total syntheses of the cyclopeptide alkaloids paliurine E and F, ziziphine N and Q, abyssenine A, and mucronine E is provided. A key feature of the syntheses involves an intramolecular amidation of a vinyl iodide, which allows us simultaneously to address two synthetic challenges associated with cyclopeptide alkaloids: the formation of the enamide and macrocyclization. We also document the use of other strategies for the macrocyclization step, as well as the evaluation of the antibacterial and cytotoxic properties of the natural products and analogues obtained.

中文翻译:

环肽生物碱的一般途径:Paliurines E 和 F、Ziziphines N 和 Q、Abyssenine A、Mucronine E 和类似物的全合成和生物学评价

提供了环肽生物碱 paliurine E 和 F、ziziphine N 和 Q、abyssenine A 和 mucronine E 的全合成的完整说明。合成的一个关键特征涉及乙烯基碘的分子内酰胺化,这使我们能够同时解决与环肽生物碱相关的两个合成挑战:烯酰胺的形成和大环化。我们还记录了其他策略在大环化步骤中的使用,以及对获得的天然产物和类似物的抗菌和细胞毒性特性的评估。
更新日期:2009-07-01
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