Total Synthesis of Spirotryprostatins through Organomediated Intramolecular Umpolung Cyclization |
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| Authors: | Yong-Kai Xi Prof. Dr. Hongbin Zhang Rui-Xi Li Shi-Yuan Kang Jin Li Yan Li |
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| Affiliation: | 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 |
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| Abstract: | 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. |
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| Keywords: | alkaloids cascade cyclization spirotryprostatins total synthesis umplolung cyclization |
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