The versatility of the natural products (2S,3S)- and (2S,3R)-3-hydroxy-5-oxotetrahydrofuran-2,3-dicarboxylic acids (1 and 2), isolated in large amounts from tropical plant sources, has been demonstrated by the construction of 3-substituted and 3,4-disubstituted chiral pyrrolidine-2,5-diones. The absolute configurations of chiral pyrrolidine-2,5-diones have been ascertained using chiroptical spectroscopic methods and/or single-crystal XRD data. A combination of different reaction strategies delivering a diverse matrix of fused heterocyclic ring systems is presented. The pyrrolo[2,1-a]isoquinoline alkaloid (+)-crispine A possesses a wide range of pharmacological activities including antidepressant, antiplatelet, antileukemic, and anticancer activities. The analogues of indolizino[8,7-b]indole alkaloids (+)- and (−)-harmicine show strong antileishmanial, antinociceptive, PDE5-inhibitory, antimalarial, and antiviral activities. The bicyclic furo[2,3-b]pyrrolo skeleton is present in many natural products. Thus, the uniqueness of relatively cheap, naturally occurring chiral 2-hydroxycitric acid lactones as chirons has been demonstrated by the construction of some important molecular skeletons that are otherwise difficult to synthesize.

中文翻译：

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天然产物衍生的手性吡咯烷-2,5-二酮、它们的分子结构和向药理学上重要骨架的转化。

从热带植物中大量分离的天然产物 (2 S ,3 S )- 和 (2 S ,3 R )-3-羟基-5-氧代四氢呋喃-2,3-二羧酸（1和2）的多功能性来源，已通过构建 3-取代和 3,4-二取代手性吡咯烷-2,5-二酮证明。手性吡咯烷-2,5-二酮的绝对构型已使用手性光谱方法和/或单晶 XRD 数据确定。提出了提供不同稠合杂环系统矩阵的不同反应策略的组合。吡咯[2,1- a]异喹啉生物碱 (+)-crispine A 具有广泛的药理活性，包括抗抑郁、抗血小板、抗白血病和抗癌活性。indolizino[8,7- b ]indole 生物碱 (+)- 和 (-)-harmicine 的类似物显示出很强的抗利什曼原虫、镇痛、PDE5 抑制、抗疟和抗病毒活性。双环呋喃[2,3- b ]吡咯骨架存在于许多天然产物中。因此，相对便宜的、天然存在的手性 2-羟基柠檬酸内酯作为 chirons 的独特性已通过构建一些否则难以合成的重要分子骨架得到证明。