Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5218856 | Tetrahedron | 2012 | 4 Pages |
Abstract
A concise synthesis of zanamivir (GG167, 1) has been accomplished utilizing the adduct of a highly diastereoselective 1,3-dipolar cycloaddition between methyl acrylate and the nitrone derived from d-glucono-δ-lactone. Azide-free introduction of C4 nitrogen functionality and one-pot selective O-acetylation followed by straightforward generation of dihydropyran moiety are two advantages in this synthesis. Using the established methodology and common intermediate, two representative C4-thiocarbamido derivatives of zanamivir were also synthesized.
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Physical Sciences and Engineering
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Organic Chemistry
Authors
Xue-Bin Zhu, Meng Wang, Shaozhong Wang, Zhu-Jun Yao,