通过有机介导的分子内反转环化反应全合成螺环三肽菌素。
Total Synthesis of Spirotryprostatins through Organomediated Intramolecular Umpolung Cyclization.
机构信息
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan province, State Key Laboratory for, Conservation and Utilization of Bio-Resources in Yunnan, School of, Chemical Science and Technology, Yunnan University, Kunming, Yunnan, 650091, P. R. China.
出版信息
Chemistry. 2019 Feb 26;25(12):3005-3009. doi: 10.1002/chem.201806411. Epub 2019 Jan 29.
Cyclodipeptide 2,5-diketopiperazines (DKP) are privileged structural units present in drugs and natural alkaloids. This work reports a new method for the synthesis of biologically important DKP scaffolds based on an intramolecular nucleophilic α-addition of general amides towards an alkynamide system. The utility of this umpolung cyclization mediated by trimethyl phosphine and l-glutamic acid is highlighted by its application to the concise total syntheses of 6-methoxyspirotryprostatin B (the first total synthesis), spirotryprostatin A, and spirotryprostatin B.
环二肽 2,5-二酮哌嗪（DKP）是存在于药物和天然生物碱中的重要结构单元。本工作报道了一种基于一般酰胺对炔酰胺体系的分子内亲核 α-加成反应合成具有生物重要性的 DKP 支架的新方法。三甲基膦和 L-谷氨酸介导的这种反转环化反应的实用性通过其在 6-甲氧基螺普罗托菌素 B（首次全合成）、螺普罗托菌素 A 和螺普罗托菌素 B 的简洁全合成中的应用得到了强调。
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