{"title":"A synthesis of L-(+)-quinic acid from D-(–)-quinic acid","authors":"Johnny Nguyen, Sandeep Bhosale, Andrew J. Bennet","doi":"10.1139/cjc-2023-0139","DOIUrl":null,"url":null,"abstract":"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.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"14 5","pages":""},"PeriodicalIF":1.1000,"publicationDate":"2023-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Canadian Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1139/cjc-2023-0139","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
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Abstract
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.
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.
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