Institute for Integrated Programmes and Research in Basic Sciences, Mahatma Gandhi University, Kottayam 686560, India.
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States.
J Nat Prod. 2020 Jul 24;83(7):2178-2190. doi: 10.1021/acs.jnatprod.0c00211. Epub 2020 Jun 25.
The versatility of the natural products (2,3)- and (2,3)-3-hydroxy-5-oxotetrahydrofuran-2,3-dicarboxylic acids ( and ), 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-]isoquinoline alkaloid (+)-crispine A possesses a wide range of pharmacological activities including antidepressant, antiplatelet, antileukemic, and anticancer activities. The analogues of indolizino[8,7-]indole alkaloids (+)- and (-)-harmicine show strong antileishmanial, antinociceptive, PDE5-inhibitory, antimalarial, and antiviral activities. The bicyclic furo[2,3-]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.
从热带植物资源中大量分离出的天然产物 (2,3)- 和 (2,3)-3-羟基-5-氧代四氢呋喃-2,3-二羧酸 () 和 ，其多功能性已通过构建 3-取代和 3,4-二取代手性吡咯烷-2,5-二酮得到证明。使用手性光谱方法和/或单晶 XRD 数据确定了手性吡咯烷-2,5-二酮的绝对构型。本文提出了一种结合了不同反应策略的方法，可提供多样化的稠合杂环体系矩阵。吡咯并[2,1-]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。吲哚利嗪[8,7-]吲哚生物碱 (+)-和 (-)-harmicine 的类似物具有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-]吡咯骨架存在于许多天然产物中。因此，相对廉价、天然存在的手性 2-羟基柠檬酸内酯作为手性中心的独特性已通过构建一些原本难以合成的重要分子骨架得到证明。
