Stereoselective Synthesis of Baloxavir Marboxil Using Diastereoselective Cyclization and Photoredox Decarboxylation of l-Serine

Baloxavir marboxil (1; BXM) is a potent drug used for treating influenza infections. The current synthetic route to BXM (1) is based on optical resolution; however, this method results in the loss of nearly 50% of the material. This study aimed to describe an efficient and simpler method for the synthesis of BXM. We achieved a stereoselective synthesis of BXM (1). The tricyclic triazinanone core possessing a chiral center was prepared via diastereoselective cyclization utilizing the readily available amino acid l-serine. The carboxyl moiety derived from l-serine was removed via photoredox decarboxylation under mild conditions to furnish the chiral tricyclic triazinanone core ((R)-14). The synthetic route demonstrated herein provides an efficient and atomically economical method for preparing this potent anti-influenza agent.

• Okamoto, K
• Ueno, T
• Hato, Y
• Kawaguchi, Y
• Hakogi, T
• Majima, S
• Ohara, T
• Hagihara, M
• Tanimoto, N
• Tsuritani, T

• Technology Development Division, Shionogi Pharma & Co., Ltd., 1-3, Kuise Terajima 2-Chome, Amagasaki, Hyogo 660-0813, Japan

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