通过（2,4）-4-羟基谷氨酸内酯的克级合成实现萱草属色胺 I 的全合成。
Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2,4)-4-Hydroxyglutamic Acid Lactone.
机构信息
Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia.
Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40 Prague, Czech Republic.
出版信息
Molecules. 2023 Feb 26;28(5):2177. doi: 10.3390/molecules28052177.
Total synthesis of the 2-formylpyrrole alkaloid hemerocallisamine I is presented, both in racemic and enantiopure form. Our synthetic strategy involves (2,4)-4-hydroxyglutamic acid lactone as the key intermediate. Starting from an achiral substrate, the target stereogenic centers were introduced by means of crystallization-induced diastereomer transformation (CIDT) in a highly stereoselective fashion. A Maillard-type condensation was crucial to constructing the desired pyrrolic scaffold.
本文呈现了 2-甲酰基吡咯生物碱萱草根素 I 的全合成，包括外消旋体和对映纯体形式。我们的合成策略涉及（2,4）-4-羟基谷氨酸内酯作为关键中间体。从一个非手性底物开始，通过结晶诱导的非对映异构体转化（CIDT）以高度立体选择性的方式引入目标立体中心。美拉德型缩合对于构建所需的吡咯骨架至关重要。
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