从 D-(-)-奎宁酸合成 L-(+)-奎宁酸

IF 1.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Canadian Journal of Chemistry Pub Date : 2023-11-17 DOI:10.1139/cjc-2023-0139

Johnny Nguyen, Sandeep Bhosale, Andrew J. Bennet

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引用次数: 0

摘要

在此，我们报告了以天然产物 D-(-)-奎宁酸为原料，通过十二个步骤高效合成 L-(+)-奎宁酸的过程。关键步骤包括利用优化的氧化-还原条件，对内酯中间体进行动力学控制的选择性保护，并反转两个立体中心：喹酸核心的 C-3 和 C-5 羟基。

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A synthesis of L-(+)-quinic acid from D-(–)-quinic acid

Here, we report an efficient synthesis of L-(+)-quinic acid from the natural product D-(–)-quinic acid in a twelve-step sequence. The key steps involve the kinetic controlled selective protection of a lactone intermediate and the inversion of two stereocentres: the C-3 and C-5 hydroxyl of the quinic acid core using optimized oxidation-reduction conditions.

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来源期刊

Canadian Journal of Chemistry 化学-化学综合

CiteScore

1.90

自引率

9.10%

发文量

审稿时长

1 months

期刊介绍： Published since 1929, the Canadian Journal of Chemistry reports current research findings in all branches of chemistry. It includes the traditional areas of analytical, inorganic, organic, and physical-theoretical chemistry and newer interdisciplinary areas such as materials science, spectroscopy, chemical physics, and biological, medicinal and environmental chemistry. Articles describing original research are welcomed.