{"title":"Ce(OTf)3-Catalyzed Synthesis of Glucopyranurono-6,1-Lactone: A Key Intermediate for Obtaining Glycoconjugates of Peptidic Fragments of Arenastatin A","authors":"A. Mezrai, L. Mrah, Z. Khiati, A. Keniche","doi":"10.2174/0115701786325021240817182955","DOIUrl":null,"url":null,"abstract":"In this work, 2,3,4-tri-O-acetyl-D-glucurono-6,1-lactone has been prepared from glucuronic acid in two steps by converting it into glucuronic anhydride. In the presence of a catalytic amount of Ce(OTf)3 (10 examples) in ethyl acetate, the glucuronic anhydride provided 6.1-lactone in good to excellent yields. This lactone was used to prepare the novel glycoconjugates of peptidic fragments of arenastatin A, a sponge cytotoxic depsipeptide, and its analogues.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"27 1","pages":""},"PeriodicalIF":0.7000,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Letters in Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.2174/0115701786325021240817182955","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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Abstract
In this work, 2,3,4-tri-O-acetyl-D-glucurono-6,1-lactone has been prepared from glucuronic acid in two steps by converting it into glucuronic anhydride. In the presence of a catalytic amount of Ce(OTf)3 (10 examples) in ethyl acetate, the glucuronic anhydride provided 6.1-lactone in good to excellent yields. This lactone was used to prepare the novel glycoconjugates of peptidic fragments of arenastatin A, a sponge cytotoxic depsipeptide, and its analogues.
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Letters in Organic Chemistry publishes original letters (short articles), research articles, mini-reviews and thematic issues based on mini-reviews and short articles, in all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is to publish quality papers rapidly by taking full advantage of latest technology for both submission and review of the manuscripts.
The journal is an essential reading for all organic chemists belonging to both academia and industry.
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