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

被引：0

作者：

Mezrai, A. ^{[1
,2
]}

Mrah, L. ^{[2
,3
]}

Khiati, Z. ^{[3
]}

Keniche, A. ^{[1
]}

机构：

[1] Univ Tlemcen, Lab Organ Chem Nat Prod & Anal, POB 119, Tilimsen 13000, Algeria

[2] Ecole Super Genie Elect & Energet Oran, Chemin Vin 9, Oran, Algeria

[3] Univ Sci & Technol Oran Mohamed Boudiaf, Fac Chim, Dept Genie Chim, USTO MB,Lab Synth Organ Physicochim Biomol & Envir, BP 1505, Oran 31000, Algeria

来源：

LETTERS IN ORGANIC CHEMISTRY | 2024年

关键词：

Glucuronic acid; depsipeptide; glycoconjugate; arenastatin A; catalysis; cytotoxicity; anticancer; POTENT CYTOTOXIC DEPSIPEPTIDE; CRYPTOPHYCIN ANALOGS; GLUCURONIC-ACID; ENANTIOSELECTIVE SYNTHESIS; CHEMOENZYMATIC SYNTHESIS; BIOLOGICAL EVALUATION; ANTITUBULIN ACTIVITY; UNIT-B; EFFICIENT; DESIGN;

D O I：

10.2174/0115701786325021240817182955

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：317 / 326

页数：9

共 82 条

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