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Letters in Organic Chemistry

Author(s): A. Mezrai*, L. Mrah, Z. Khiati and A. Keniche

DOI: 10.2174/0115701786325021240817182955

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Ce(OTf)3-Catalyzed Synthesis of Glucopyranurono-6,1-Lactone: A Key Intermediate for Obtaining Glycoconjugates of Peptidic Fragments of Arenastatin A

Page: [317 - 326] Pages: 10

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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.

Keywords: Glucuronic acid, depsipeptide, glycoconjugate, arenastatin A, catalysis, cytotoxicity, anticancer.