Synthesis of Remdesivir by Direct Lithiation of Pyrrolotriazine Derivatives Enabled C‐Glycosylation

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Synthesis of Remdesivir by Direct Lithiation of Pyrrolotriazine Derivatives Enabled C‐Glycosylation

Xu, Chao; Yu‐Han Hu; He, Yong; Hu, Zhigang; Li, Shikuo; Zhang, Hui; Huang, Fangzhi; Feng‐Lian Zhang; Yue‐Lei Chen

European journal of organic chemistry, 06/2023, Volume: 26, Issue: 24

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A direct and regioselective lithiation was realized on N‐Boc‐pyrrolo2,1‐f1,2,4triazine, simply utilizing the distinct sigma‐acidity on C‐9. Starting from this enabling discovery, C‐glycoside formation, cyanation, and global deprotection steps constitute one of the most efficient syntheses of GS‐441524. Furthermore, transient protection was applied on GS‐441524 with phenyl boronic acid, which facilitated a powerful one‐pot synthesis of remdesivir.

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