Stereoselective Synthesis of Baloxavir Marboxil Using Diastereoselective Cyclization and Photoredox Decarboxylation of l-Serine.
J Org Chem
; 89(14): 9937-9948, 2024 07 19.
Article
en En
| MEDLINE
| ID: mdl-38985331
ABSTRACT
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.
Texto completo:
1
Base de datos:
MEDLINE
Asunto principal:
Serina
/
Dibenzotiepinas
Idioma:
En
Revista:
J Org Chem
/
J. org. chem
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Journal of organic chemistry
Año:
2024
Tipo del documento:
Article